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1. 发明授权

US07541456B2 Direct, enantioselective aldol coupling of aldehydes using chiral organic catalysts 失效
标题翻译：使用手性有机催化剂的醛的直接，对映选择性醛醇偶联
公开(公告)号：US07541456B2
公开(公告)日：2009-06-02
申请号：US11112309
申请日：2005-04-21
申请人： David W. C. MacMillan , Alan B. Northrup
发明人： David W. C. MacMillan , Alan B. Northrup
IPC分类号： C07H3/00
CPC分类号： C07D309/10 , C07B2200/07 , C07C29/143 , C07C45/72 , C07C2601/14 , C07C47/27 , C07C47/192 , C07C47/19 , C07C33/025 , C07C33/035 , C07C33/14 , C07C33/30
摘要： Nonmetallic, chiral organic catalysts are used to catalyze an enantioselective aldol coupling reaction between aldehyde substrates. The reaction may be carried out with a single enolizable aldehyde, resulting in dimerization to give a β-hydroxy aldehyde, or trimerization to give a dihydroxy tetrahydropyran. The reaction may also conducted with an enolizable aldehyde and a second aldehyde, which may or may not be enolizable, so that the coupling is a cross-aldol reaction in which the α-carbon of the enolizable aldehyde adds to the carbonyl carbon of the second aldehyde in an enantioselective fashion. Reaction systems composed of at least one enolizable aldehyde, an optional additional aldehyde, and the nonmetallic chiral organic catalyst are also provided, as are methods of implementing the enantioselective aldol reaction in the synthesis of sugars.
摘要翻译：非金属手性有机催化剂用于催化醛底物之间的对映选择性醛醇偶联反应。该反应可以用单一可烯化的醛进行，导致二聚化得到β-羟基醛，或三聚反应得到二羟基四氢吡喃。该反应也可以用可烯化的醛和第二个醛进行，其可以是或不可烯化的，使得偶联是交叉醛醇缩合反应，其中可烯化的醛的α-碳加到第二个的羰基碳上醛以对映选择性方式。还提供由至少一种可烯化醛，任选的另外的醛和非金属手性有机催化剂组成的反应体系，以及在合成糖中实施对映选择性醛醇反应的方法。

2. 发明授权

US07592463B2 Enantioselective transformation of α,β-unsaturated ketones using chiral organic catalysts 有权
标题翻译：使用手性有机催化剂对α，β-不饱和酮的对映选择性转化
公开(公告)号：US07592463B2
公开(公告)日：2009-09-22
申请号：US10313744
申请日：2002-12-05
申请人： David W. C. MacMillan , Alan B. Northrup
发明人： David W. C. MacMillan , Alan B. Northrup
IPC分类号： C07D233/28 , C07D235/02 , C07C45/69
CPC分类号： C07D405/04 , B01J31/0237 , B01J31/0247 , B01J2231/326 , C07B2200/07 , C07C45/69 , C07C49/543 , C07C49/553 , C07C49/557 , C07C49/577 , C07C49/643 , C07C269/06 , C07D233/32 , C07C271/24
摘要： Nonmetallic organic catalysts are provided that facilitate the enantioselective reaction of α,β-unsaturated ketones. The catalysts are chiral imidazolidinone compounds having the structure of formula (IIA) or (IIB) or are acid addition salts thereof, wherein, in one preferred embodiment, R1 is C1-C6 alkyl, R2 is phenyl or 2-methylfuryl, R3 and R4 are hydrogen, and R5 is phenyl optionally substituted with 1 or 2 substituents selected from the group consisting of halo, hydroxyl, and C1-C6 alkyl. The chiral imidazolidinones are useful in catalyzing a wide variety of reactions, including cycloaddition reactions, Friedel-Crafts alkylation reactions, and Michael additions.
摘要翻译：提供了促进α，β-不饱和酮的对映选择性反应的非金属有机催化剂。催化剂是具有式（IIA）或（IIB）结构的手性咪唑烷酮化合物或其酸加成盐，其中在一个优选的实施方案中，R 1是C 1 -C 6烷基，R 2是苯基或2-甲基呋喃基，R 3和R 4 是氢，R5是任选被1或2个选自卤素，羟基和C 1 -C 6烷基的取代基取代的苯基。手性咪唑烷酮可用于催化多种反应，包括环加成反应，Friedel-Crafts烷基化反应和迈克尔加成。

3. 发明授权

US06900357B2 Direct, enantioselective aldol coupling of aldehydes using chiral organic catalysts 失效
公开(公告)号：US06900357B2
公开(公告)日：2005-05-31
申请号：US10420339
申请日：2003-04-21
申请人： David W. C. MacMillan , Alan B. Northrup
发明人： David W. C. MacMillan , Alan B. Northrup
IPC分类号： C07C29/143 , C07C45/72 , C07D309/10
CPC分类号： C07D309/10 , C07B2200/07 , C07C29/143 , C07C45/72 , C07C2601/14 , C07C47/27 , C07C47/192 , C07C47/19 , C07C33/025 , C07C33/035 , C07C33/14 , C07C33/30
摘要： Nonmetallic, chiral organic catalysts are used to catalyze an enantioselective aldol coupling reaction between aldehyde substrates. The reaction may be carried out with a single enolizable aldehyde, resulting in dimerization to give a β-hydroxy aldehyde, or trimerization to give a dihydroxy tetrahydropyran. The reaction may also conducted with an enolizable aldehyde and a second aldehyde, which may or may not be enolizable, so that the coupling is a cross-aldol reaction in which the α-carbon of the enolizable aldehyde adds to the carbonyl carbon of the second aldehyde in an enantioselective fashion. Reaction systems composed of at least one enolizable aldehyde, an optional additional aldehyde, and the nonmetallic chiral organic catalyst are also provided, as are methods of implementing the enantioselective aldol reaction in the synthesis of sugars.

4. 发明授权

US07265249B2 Enantioselective alpha-fluorination of aldehydes using chiral organic catalysts 有权
标题翻译：使用手性有机催化剂对醛选择性α-氟化醛
公开(公告)号：US07265249B2
公开(公告)日：2007-09-04
申请号：US11334997
申请日：2006-01-18
申请人： David W. C. MacMillan , Teresa D. Beeson
发明人： David W. C. MacMillan , Teresa D. Beeson
IPC分类号： C07C45/63
CPC分类号： C07C29/64 , C07B39/00 , C07B2200/07 , C07B2200/09 , C07C45/63 , C07C47/115 , C07C67/31 , C07C2601/14 , C07C2603/74 , C07C47/24 , C07C69/675 , C07C31/38 , C07C33/423 , C07C31/44
摘要： Nonmetallic, chiral organic catalysts are used to catalyze enantioselective fluorination of enolizable aldehydes. Reaction systems composed of an enolizable aldehyde, an electrophilic fluorination reagent, and a nonmetallic chiral catalyst in the form of an imidazolidinone salt are also provided.
摘要翻译：非金属，手性有机催化剂用于催化可烯化醛的对映选择性氟化。还提供了由可烯化醛，亲电子氟化试剂和咪唑啉酮形式的非金属手性催化剂组成的反应体系。

5. 发明授权

US06369243B1 Chemical transformation of substrates using nonmetallic, organic catalyst compositions 有权
标题翻译：使用非金属有机催化剂组合物对基材进行化学转化
公开(公告)号：US06369243B1
公开(公告)日：2002-04-09
申请号：US09484082
申请日：2000-01-18
申请人： David W. C. MacMillan , Kateri A. Ahrendt
发明人： David W. C. MacMillan , Kateri A. Ahrendt
IPC分类号： C07D49308
CPC分类号： C07D493/08 , B01J31/0237 , B01J31/0254 , B01J2231/325 , B01J2231/326 , B01J2231/348 , B01J2231/72 , C07B37/12 , C07B53/00 , C07C45/69 , C07C67/293 , C07D233/32 , C07D307/46 , C07C47/445 , C07C47/453 , C07C49/453 , C07C47/42 , C07C69/013 , C07C69/145
摘要： A method is provided for catalytically transforming a functional group within a first reactant by reaction with a second reactant in the presence of a nonmetallic, organic catalyst composition composed of a heteroatom-containing activator and an acid, or a salt of a heteroatom-containing activator and an acid. Exemplary first reactants are &agr;,&bgr;-unsaturated carbonyl compounds such as &agr;,&bgr;-unsaturated ketones and &agr;,&bgr;-unsaturated aldehydes. The heteroatom of the activator is a Group 15 or Group 16 element such as nitrogen, oxygen, sulfur or phosphorus, and exemplary heteroatom-containing activators are amines. Chiral heteroatom-containing activators can be used to catalyze enantioselective reactions, such that a chiral product is obtained from a chiral or achiral starting material in enantiomerically pure form.
摘要翻译：提供了一种通过在由含杂原子的活化剂和酸或含有杂原子的活化剂的盐组成的非金属有机催化剂组合物存在下与第二反应物反应来在第一反应物内催化转化官能团的方法和酸。示例性的第一反应物是α，β-不饱和羰基化合物，例如α，β-不饱和酮和α，β-不饱和醛。活化剂的杂原子是第15族或第16族元素，例如氮，氧，硫或磷，并且示例性的含杂原子的活化剂是胺。手性含杂原子的活化剂可用于催化对映选择性反应，使得手性产物以手性或非手性起始原料以对映体纯的形式获得。

6. 发明授权

US06552226B1 Tandem acyl-Claisen rearrangement in the preparation of chiral products 失效
标题翻译：串联酰基Claisen重排在手性产物的制备中
公开(公告)号：US06552226B1
公开(公告)日：2003-04-22
申请号：US09670861
申请日：2000-09-26
申请人： David W. C. MacMillan
发明人： David W. C. MacMillan
IPC分类号： C07C23300
CPC分类号： C07D209/48 , C07D263/14 , C07D295/185
摘要： A novel tandem acyl-Claisen rearrangement reaction is provided. An allylic reactant such as an allylic amine or an allylic thioether, having at least two functional groups that enable the reactant to undergo at least two successive Claisen rearrangement reactions, is reacted with an acid chloride in the presence of a Lewis acid catalyst composition composed of a Lewis acid and a second catalyst component selected from the group consisting of tertiary amines and non-nitrogenous bases. The stereochemistry of the reaction product is readily controlled by the positioning and size of substituents on the allylic reactant. The reaction may be carried out on a solid support, i.e., on the surface of a substrate suitable for conducting solid phase chemical reactions.
摘要翻译：提供了一种新的串联酰基 - 克莱森重排反应。具有至少两个能够使反应物经历至少两次连续克莱森重排反应的官能团的烯丙基反应物如烯丙基胺或烯丙基硫醚与酰基氯在路易斯酸催化剂组合物的存在下反应，路易斯酸催化剂组合物由路易斯酸和选自叔胺和非含氮碱的第二催化剂组分。反应产物的立体化学通过烯丙基反应物上取代基的定位和大小容易地控制。反应可以在固体载体上，即在适于进行固相化学反应的基材的表面上进行。

7. 发明授权

US06359174B1 Lewis acid-catalyzed claisen rearrangement in the preparation of chiral products 失效
标题翻译：路易斯酸催化的claisen重排在手性产物的制备中
公开(公告)号：US06359174B1
公开(公告)日：2002-03-19
申请号：US09670863
申请日：2000-09-26
申请人： David W. C. MacMillan , Vy Dong , Tehshik Yoon
发明人： David W. C. MacMillan , Vy Dong , Tehshik Yoon
IPC分类号： C07C23102
CPC分类号： C07D295/185 , C07B2200/07 , C07D263/32 , C07D295/182
摘要： A novel Claisen rearrangement reaction is provided. An allylic reactant such as an allylic amine, an allylic ether or an allylic thioether is reacted with an acid chloride in the presence of a Lewis acid catalyst composition composed of a Lewis acid and a base selected from the group consisting of tertiary amines and non-nitrogenous bases. The stereochemistry of the reaction product is readily controlled by the positioning and size of substituents on the allylic reactant. The reaction may be carried out on a solid support, i.e., on the surface of a substrate suitable for conducting solid phase chemical reactions.
摘要翻译：提供了一种新的Claisen重排反应。烯丙基胺，烯丙基醚或烯丙基硫醚等烯丙基反应物与酰氯在路易斯酸催化剂组合物的存在下反应，路易斯酸催化剂组合物由路易斯酸和选自叔胺，含氮碱。反应产物的立体化学通过烯丙基反应物上取代基的定位和大小容易地控制。反应可以在固体载体上，即在适于进行固相化学反应的基材的表面上进行。

8. 发明授权

US06307057B1 Acid addition salts of imidazolidinones as reaction catalysts 有权
标题翻译：咪唑啉酮的酸加成盐作为反应催化剂
公开(公告)号：US06307057B1
公开(公告)日：2001-10-23
申请号：US09547958
申请日：2000-04-12
申请人： David W. C. MacMillan , Kateri A. Ahrendt
发明人： David W. C. MacMillan , Kateri A. Ahrendt
IPC分类号： C07D23332
CPC分类号： C07D493/08 , B01J31/0237 , B01J31/0254 , B01J2231/325 , B01J2231/326 , B01J2231/348 , B01J2231/72 , C07B37/12 , C07B53/00 , C07C45/69 , C07C67/293 , C07D233/32 , C07D307/46 , C07C47/445 , C07C47/453 , C07C49/453 , C07C47/42 , C07C69/013 , C07C69/145
摘要： Acid addition salts of imidazolidinones are provided as catalysts for transforming a functional group within a first reactant by reaction with a second reactant. Exemplary first reactants are &agr;,&bgr;-unsaturated carbonyl compounds such as &agr;,&bgr;-unsaturated ketones and &agr;,&bgr;-unsaturated aldehydes. Chiral imidazolidinone salts can be used to catalyze enantioselective reactions, such that a chiral product is obtained from a chiral or achiral starting material in enantiomerically pure form.
摘要翻译：提供咪唑啉酮的酸加成盐作为用于通过与第二反应物反应转化第一反应物中的官能团的催化剂。示例性的第一反应物是α，β-不饱和羰基化合物，例如α，β-不饱和酮和α，β-不饱和醛。手性咪唑烷酮盐可用于催化对映选择性反应，使得手性产物以手性或非手性起始原料以对映体纯的形式获得。

9. 发明授权

US07173139B2 Enantioselective 1,4-addition of aromatic nucleophiles to α,β-unsaturated aldehydes using chiral organic catalysts 失效
标题翻译：使用手性有机催化剂将芳香族亲核试剂对映选择性1,4-加成α，β-不饱和醛
公开(公告)号：US07173139B2
公开(公告)日：2007-02-06
申请号：US10394758
申请日：2003-03-21
申请人： David W. C. MacMillan , Nick A. Paras
发明人： David W. C. MacMillan , Nick A. Paras
IPC分类号： C07D233/00 , C07C45/00
CPC分类号： C07D207/333 , C07B2200/07 , C07C45/69 , C07C327/22 , C07D209/12 , C07D209/18 , C07D209/22 , C07D209/24 , C07D233/32 , C07D261/02 , C07D295/155 , C07D307/58 , C07D311/20 , C07D333/32 , C07D487/04 , C07C47/453 , C07C47/445
摘要： Nonmetallic, chiral organic catalysts are used to catalyze the 1,4-addition of an aromatic nucleophile to an α,β-unsaturated aldehyde. The aromatic nucleophile may be an N,N-disubstituted aniline compound, or an analog thereof. The reaction is efficient and enantioselective, and proceeds with a variety of substituted and unsubstituted aromatic nucleophiles and aldehydes. The invention also provides a method for the deamination of aromatic N,N-disubstituted amines such as those resulting from the 1,4-addition of an aromatic nucleophile to an α,β-unsaturated aldehyde.
摘要翻译：非金属手性有机催化剂用于催化芳族亲核试剂向α，β-不饱和醛的1,4-加成。芳族亲核试剂可以是N，N-二取代的苯胺化合物或其类似物。该反应是有效的和对映选择性的，并且进行各种取代和未取代的芳族亲核试剂和醛。本发明还提供了芳族N，N-二取代的胺脱氨基的方法，例如由芳香族亲核试剂1,4-加成到α，β-不饱和醛中的那些。

10. 发明授权

US06784323B2 Enantioselective transformation of &agr;,&bgr;-unsaturated aldehydes using chiral organic catalysts 有权
标题翻译：使用手性有机催化剂对α，β-不饱和醛的对映选择性转化
公开(公告)号：US06784323B2
公开(公告)日：2004-08-31
申请号：US10187635
申请日：2002-07-01
申请人： David W. C. MacMillan
发明人： David W. C. MacMillan
IPC分类号： C07C4500
CPC分类号： C07D207/333 , C07B2200/07 , C07C45/69 , C07C327/22 , C07D209/12 , C07D209/18 , C07D209/22 , C07D209/24 , C07D233/32 , C07D261/02 , C07D295/155 , C07D307/58 , C07D311/20 , C07D333/32 , C07D487/04 , C07C47/453 , C07C47/445
摘要： Nonmetallic organic catalysts are provided that facilitate the enantioselective reaction of &agr;,&bgr;-unsaturated aldehydes. The catalysts are chiral imidazolidinone compounds having the structure of formula (IIA) or (IIB) or are acid addition salts thereof, wherein, in one preferred embodiment, R1 is C1-C6 alkyl, R2 is tri(C1-C6 alkyl)-substituted methyl, R3 and R4 are hydrogen, and R5 is phenyl optionally substituted with 1 or 2 substituents selected from the group consisting of halo, hydroxyl, and C1-C6 alkyl. The chiral imidazolidinones are useful in catalyzing a wide variety of reactions, including cycloaddition reactions, Friedel-Crafts alkylation reactions, and Michael additions.
摘要翻译：提供非金属有机催化剂，促进α，β-不饱和醛的对映选择性反应。催化剂是具有式（IIA）或（IIB）结构的手性咪唑烷酮化合物或其酸加成盐，其中在一个优选的实施方案中，R 1是C 1 -C 6烷基，R 2是三（C1 -C 6烷基）取代的甲基，R 3和R 4为氢，R 5为任选被1或2个选自卤素，羟基和C 1 -C 6烷基的取代基取代的苯基。手性咪唑烷酮可用于催化多种反应，包括环加成反应，Friedel-Crafts烷基化反应和迈克尔加成。

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