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1. 发明申请

US20120101309A1 OPTICALLY ACTIVE QUATERNARY AMMONIUM SALT HAVING AXIAL ASYMMETRY, AND METHOD FOR PRODUCING ALPHA-AMINO ACID AND DERIVATIVE THEREOF BY USING THE SAME 审中-公开
标题翻译：具有轴向不对称性的光学活性季铵盐，以及通过使用它们生产α-氨基酸及其衍生物的方法
公开(公告)号：US20120101309A1
公开(公告)日：2012-04-26
申请号：US13338301
申请日：2011-12-28
申请人： Keiji MARUOKA , Kenichiro YAMAMOTO , Yukifumi NISHIMOTO
发明人： Keiji MARUOKA , Kenichiro YAMAMOTO , Yukifumi NISHIMOTO
IPC分类号： C07C43/225
CPC分类号： C07B53/00 , B01J31/0239 , B01J2231/46 , B01J2531/0266 , B01J2531/985 , C07B2200/07 , C07C43/225 , C07C249/02 , C07D223/18 , C07D487/04 , C07C251/24
摘要： The present invention discloses an optically active quanternary ammonium salt having axial asymmetry and a method for producing an α-amino acid and a derivative thereof using the same. The optically active quanternary ammonium salt having axial asymmetry of the present invention is a chiral phase-transfer catalyst that has a simple structure and that can be produced in a smaller number of process steps. The compound of the present invention is very useful as a phase-transfer catalyst in the synthesis of an α-alkyl-α-amino acid and a derivative thereof as well as an α,α-dialkyl-α-amino acid and a derivative thereof. Therefore, the compound of the present invention can be used in the development of novel foods and pharmaceuticals.
摘要翻译：本发明公开了具有轴向不对称性的光学活性季铵盐和使用其制备α-氨基酸及其衍生物的方法。具有本发明的轴向不对称性的光学活性季铵盐是手性相转移催化剂，其具有简单的结构，并且可以以较少数量的工艺步骤生产。本发明的化合物在α-烷基-α-氨基酸及其衍生物以及α，α-二烷基-α-氨基酸及其衍生物的合成中作为相转移催化剂是非常有用的。因此，本发明的化合物可用于开发新型食品和药物。

2. 发明申请

US20070161624A1 Optically active quaternary ammonium salt having axial asymmetry and process for producing alpha-amino acid and derivative thereof with the same 有权
标题翻译：具有轴向不对称性的光学活性季铵盐及其制备α-氨基酸及其衍生物的方法
公开(公告)号：US20070161624A1
公开(公告)日：2007-07-12
申请号：US10587467
申请日：2005-01-27
申请人： Keiji Maruoka
发明人： Keiji Maruoka
IPC分类号： A61K31/55 , C07D223/14
CPC分类号： C07D223/14 , B01J31/0237 , B01J31/0239 , B01J2231/4272 , B01J2531/98 , C07C229/36 , C07D405/14 , C07D409/14 , C07D471/10 , C07D487/10
摘要： The present invention provides a compound of the following formula (I) below. This compound (I) can be produced by reacting a 2,2′-dimethylene bromide-1,1′-binaphthyl derivative, which can be produced by a relatively small number of processes, with an easily available secondary amine. This compound (I) is useful as a chiral phase-transfer catalyst.
摘要翻译：本发明提供下述式（I）的化合物。该化合物（I）可以通过使可通过相对少量方法制备的2,2'-二亚甲基溴-1,1'-联萘衍生物与容易获得的仲胺反应来制备。该化合物（I）可用作手性相转移催化剂。

3. 发明申请

US20060069134A1 Process for producing optically active alpha-substituted cysteine or salt thereof, intermediate therefor, and process for producing the same 审中-公开
标题翻译：用于制备光学活性α-取代的半胱氨酸或其盐的方法及其制备方法
公开(公告)号：US20060069134A1
公开(公告)日：2006-03-30
申请号：US10529039
申请日：2003-10-01
申请人： Keiji Maruoka , Takashi Ooi , Kenji Inoue
发明人： Keiji Maruoka , Takashi Ooi , Kenji Inoue
IPC分类号： C07D277/56 , A61K31/426 , C07F7/02
CPC分类号： B01J31/0239 , B01J31/40 , C07B2200/07 , C07C319/02 , C07D277/12 , Y02P20/584 , C07C323/58
摘要： The present invention provides a simple, practical, and industrially advantageous process for producing an optically active α-substituted cysteine or a salt thereof from inexpensive and readily available materials. The present invention provides a process for producing an optically active α-substituted cysteine or a salt thereof by converting a cysteine derivative into a thiazoline compound and subjecting the resulting thiazoline compound to a stereoselective substituent-introducing reaction catalyzed by an optically active quaternary ammonium salt, in particular, an axially asymmetric quaternary ammonium salt to produce an optically active thiazoline compound and then hydrolyzing the resulting thiazoline compound.
摘要翻译：本发明提供了一种简便，实用和工业上有用的方法，用于从廉价且易于获得的材料制备光学活性的α-取代的半胱氨酸或其盐。本发明提供了通过将半胱氨酸衍生物转化为噻唑啉化合物并使所得到的噻唑啉化合物进行由光学活性季铵盐催化的立体选择性取代基引入反应来制备光学活性α-取代的半胱氨酸或其盐的方法，特别是轴向不对称的季铵盐，以产生光学活性的噻唑啉化合物，然后水解所得的噻唑啉化合物。

4. 发明授权

US06441231B1 Optically active quarternary ammonium salt with axial chirality, method for producing thereof, and application thereof for asymmetric synthesis of &agr;-amino acid 有权
公开(公告)号：US06441231B1
公开(公告)日：2002-08-27
申请号：US09987544
申请日：2001-11-15
申请人： Keiji Maruoka
发明人： Keiji Maruoka
IPC分类号： C07C22906
CPC分类号： C07D487/10 , C07B2200/07 , C07C309/65 , C07D223/14
摘要： A novel optically active quarternary ammonium salt with an axial chirality is provided. The quarternary ammonium salt can act as a phase-transfer catalyst to convert glycine derivatives into optically active &agr;-amino acid derivatives by stereoselectively alkylating the glycine derivatives. Furthermore, according to the present invention, intermediates useful for producing the novel quarternary ammonium can be produced.

5. 发明授权

US08697910B2 Optically active quaternary ammonium salt having axial asymmetry and process for producing α-amino acid and derivative thereof with the same 有权
标题翻译：具有轴向不对称性的光学活性季铵盐及其制备α-氨基酸及其衍生物的方法
公开(公告)号：US08697910B2
公开(公告)日：2014-04-15
申请号：US11626228
申请日：2007-01-23
申请人： Keiji Maruoka
发明人： Keiji Maruoka
IPC分类号： C07C227/16
CPC分类号： C07D223/14 , B01J31/0237 , B01J31/0239 , B01J2231/4272 , B01J2531/98 , C07C229/36 , C07D405/14 , C07D409/14 , C07D471/10 , C07D487/10
摘要： The present invention provides a compound of the following formula (I) below. This compound (I) can be produced by reacting a 2,2′-dimethylene bromide-1,1′-binaphthyl derivative, which can be produced by a relatively small number of processes, with an easily available secondary amine. This compound (I) is useful as a chiral phase-transfer catalyst.
摘要翻译：本发明提供下述式（I）的化合物。该化合物（I）可以通过使可通过相对少量方法制备的2,2'-二亚甲基溴-1,1'-联萘衍生物与容易获得的仲胺反应来制备。该化合物（I）可用作手性相转移催化剂。

6. 发明申请

US20120095218A1 OPTICALLY ACTIVE QUATERNARY AMMONIUM SALT HAVING AXIAL ASYMMETRY, AND METHOD FOR PRODUCING ALPHA-AMINO ACID AND DERIVATIVE THEREOF BY USING THE SAME 审中-公开
公开(公告)号：US20120095218A1
公开(公告)日：2012-04-19
申请号：US13337658
申请日：2011-12-27
申请人： Keiji Maruoka , Kenichiro Yamamoto , Yukifumi Nishimoto
发明人： Keiji Maruoka , Kenichiro Yamamoto , Yukifumi Nishimoto
IPC分类号： C07D223/18
CPC分类号： C07B53/00 , B01J31/0239 , B01J2231/46 , B01J2531/0266 , B01J2531/985 , C07B2200/07 , C07C43/225 , C07C249/02 , C07D223/18 , C07D487/04 , C07C251/24
摘要： The present invention discloses an optically active quarternary ammonium salt having axial asymmetry and a method for producing an α-amino acid and a derivative thereof using the same. The optically active quarternary ammonium salt having axial asymmetry of the present invention is a chiral phase-transfer catalyst that has a simple structure and that can be produced in a smaller number of process steps. The compound of the present invention is very useful as a phase-transfer catalyst in the synthesis of an α-alkyl-α-amino acid and a derivative thereof as well as an α,α-dialkyl-α-amino acid and a derivative thereof. Therefore, the compound of the present invention can be used in the development of novel foods and pharmaceuticals.

7. 发明授权

US07928224B2 Optically active quaternary ammonium salt having axial asymmetry and process for producing α-amino acid and derivative thereof with the same 有权
标题翻译：具有轴向不对称性的光学活性季铵盐及其制备α-氨基酸及其衍生物的方法
公开(公告)号：US07928224B2
公开(公告)日：2011-04-19
申请号：US10587467
申请日：2005-01-27
申请人： Keiji Maruoka
发明人： Keiji Maruoka
IPC分类号： C07D223/14
CPC分类号： C07D223/14 , B01J31/0237 , B01J31/0239 , B01J2231/4272 , B01J2531/98 , C07C229/36 , C07D405/14 , C07D409/14 , C07D471/10 , C07D487/10
摘要： The present invention provides a compound of the following formula (I) below. This compound (I) can be produced by reacting a 2,2′-dimethylene bromide-1,1′-binaphthyl derivative, which can be produced by a relatively small number of processes, with an easily available secondary amine. This compound (I) is useful as a chiral phase-transfer catalyst.
摘要翻译：本发明提供下述式（I）的化合物。该化合物（I）可以通过使可通过相对少量方法制备的2,2'-二亚甲基溴-1,1'-联萘衍生物与容易获得的仲胺反应来制备。该化合物（I）可用作手性相转移催化剂。

8. 发明申请

US20090270614A1 OPTICALLY ACTIVE QUATERNARY AMMONIUM SALT HAVING AXIAL ASYMMETRY AND PROCESS FOR PRODUCING ALPHA-AMINO ACID AND DERIVATIVE THEREOF WITH THE SAME 有权
标题翻译：具有轴向不对称性的光学活性季铵盐及其制备方法与其制备氨基酸及其衍生物
公开(公告)号：US20090270614A1
公开(公告)日：2009-10-29
申请号：US11910364
申请日：2006-03-24
申请人： Keiji Maruoka , Yukifumi Nishimoto , Kenichiro Yamamoto
发明人： Keiji Maruoka , Yukifumi Nishimoto , Kenichiro Yamamoto
IPC分类号： C07D223/18 , C07C227/16 , C07C227/18
CPC分类号： C07B53/00 , B01J31/0239 , B01J2531/985 , C07C227/32 , C07C249/02 , C07D223/18 , C07D487/10 , C07C229/36 , C07C251/24
摘要： The present invention provides a chiral phase-transfer catalyst of the following formula (I): The compound (I) can be produced by reacting a 2,2′-dimethylene bromide-1,1′-biphenyl derivative, which can be produced through comparatively small number of steps, with an easily available secondary amine.
摘要翻译：本发明提供下述式（I）的手性相转移催化剂：化合物（I）可以通过使2,2'-二亚甲基溴-1,1'-联苯衍生物相对较少的步骤，具有容易获得的仲胺。

9. 发明授权

US07566779B2 Optically active quaternary ammonium salt, process for producing the same, and process for producing optically active α-amino acid derivative with the same 有权
标题翻译：光活性季铵盐，其制备方法，以及与其制备光学活性α-氨基酸衍生物的方法
公开(公告)号：US07566779B2
公开(公告)日：2009-07-28
申请号：US10563658
申请日：2004-07-22
申请人： Keiji Maruoka
发明人： Keiji Maruoka
IPC分类号： C07D223/14
CPC分类号： C07D487/10 , C07C251/24 , C07F7/081 , C07F7/0814
摘要： There are provided (1) an optically active α-amino acid derivative, a stereoselectively useful intermediate for the synthesis of pharmaceutical or agrochemical products, which derivative is an optically active quaternary ammonium salt that, when used as an axially chiral spiro phase-transfer catalyst in the asymmetric alkylation of a glycine derivative, gives a high stereoselectivity toward substrates having a small molecule such as methyl iodide, or secondary alkyl halides, and a method for producing the same; and (2) a novel optically active quaternary ammonium salt that is a high performance axially chiral spiro phase-transfer catalyst used in the asymmetric alkylation of a glycine derivative, and in which each ring of the spiro-structure has the same structure that is advantageous in terms of the number of steps involved in the synthesis of the catalyst, and a method for producing the same and a method for recovering the same.(Solving means): To achieve the objects, (1) an axially chiral spiro-ammonium salt that incorporates an alkyl- or aryl-substituted silyl group as a substituent on the aromatic ring is used as a phase-transfer catalyst in the asymmetric alkylation of a glycine derivative, and (2) an axially chiral spiro-ammonium slat that incorporates a substituent encompassing a perfluoro alkyl group is used in the asymmetric alkylation of a glycine derivative and thereafter is recovered using a fluorous solvent.
摘要翻译：提供了（1）光学活性α-氨基酸衍生物，用于合成药物或农业化学产品的立体选择性有用的中间体，该衍生物是光学活性季铵盐，当用作轴向手性螺相转移催化剂在甘氨酸衍生物的不对称烷基化中，对具有小分子的基质如甲基碘或仲烷基卤化物具有高立体选择性及其制备方法; 和（2）一种新型的光学活性季铵盐，其是用于甘氨酸衍生物的不对称烷基化的高性能轴向手性螺相转移催化剂，其中每个螺环结构的环具有相同的结构，这是有利的关于催化剂合成所涉及的步骤数及其制造方法及其回收方法。（解决方案）为了达到上述目的，（1）在芳环上含有烷基或芳基取代的甲硅烷基作为取代基的轴向手性螺 - 铵盐用作不对称烷基化中的相转移催化剂的甘氨酸衍生物，和（2）在甘氨酸衍生物的不对称烷基化中使用包含全氟烷基的取代基的轴向手性螺 - 铵板条，然后使用氟溶剂回收。

10. 发明申请

US20070135654A1 OPTICALLY ACTIVE QUATERNARY AMMONIUM SALT HAVING AXIAL ASYMMETRY AND PROCESS FOR PRODUCING alpha-AMINO ACID AND DERIVATIVE THEREOF WITH THE SAME 有权
标题翻译：具有轴向不对称的光学活性季铵盐及其生产α-氨基酸及其衍生物的方法
公开(公告)号：US20070135654A1
公开(公告)日：2007-06-14
申请号：US11626228
申请日：2007-01-23
申请人： Keiji Maruoka
发明人： Keiji Maruoka
IPC分类号： C07C229/02
CPC分类号： C07D223/14 , B01J31/0237 , B01J31/0239 , B01J2231/4272 , B01J2531/98 , C07C229/36 , C07D405/14 , C07D409/14 , C07D471/10 , C07D487/10
摘要： The present invention provides a compound of the following formula (I) below. This compound (I) can be produced by reacting a 2,2′-dimethylene bromide-1,1′-binaphthyl derivative, which can be produced by a relatively small number of processes, with an easily available secondary amine. This compound (I) is useful as a chiral phase-transfer catalyst.
摘要翻译：本发明提供下述式（I）的化合物。该化合物（I）可以通过使可通过相对少量方法制备的2,2'-二亚甲基溴-1,1'-联萘衍生物与容易获得的仲胺反应来制备。该化合物（I）可用作手性相转移催化剂。

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