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41. 发明授权

US5877343A Efficient and highly enantioselective process for the preparation of enantiomerically pure cyclopentane-.beta.-amino acids 失效
标题翻译：用于制备对映体纯的环戊烷-β-氨基酸的高效和高度对映选择性的方法
公开(公告)号：US5877343A
公开(公告)日：1999-03-02
申请号：US843102
申请日：1997-04-25
申请人： Joachim Mittendorf
发明人： Joachim Mittendorf
IPC分类号： B01J31/12 , C07B61/00 , C07C69/74 , C07C227/32 , C07C229/48 , C07C271/24 , C07C261/00 , C07C61/06 , C07C229/00
CPC分类号： C07C227/32 , C07C271/24 , C07C69/74 , C07C2101/08
摘要： The process according to the invention for the preparation of enantiomerically pure cyclopentane-.beta.-amino acids of the general formula (I) ##STR1## in which A and D have the meanings given in the description, is characterized in that meso-dicarboxylic acid anhydrides are first converted by asymmetric alcoholysis with allyl alcohols and in the presence of a chiral amine base present in enantiomerically pure form, in inert solvents, via the intermediate enantiomerically pure salt stage, into the enantiomerically pure dicarboxylic acid monoesters, in a further step these dicarboxylic acid monoesters are intermediately converted, in the sense of a Curtius rearrangement by reaction with azides, into the corresponding acid azides, and are subsequently converted into the corresponding rearranged isocyanates and the isocyanates are then reacted with allyl alcohols to give the compounds of the general formula (VII), and finally the cyclopentane-.beta.-amino acids of the general formula (I) are obtained by splitting off the urethane and ester function.
摘要翻译：根据本发明的用于制备通式（I）的对映体纯的环戊烷-β-氨基酸的方法其中A和D具有本说明书中给出的含义，其特征在于，二羧酸酐首先通过与烯丙醇的不对称醇解反应，并且在存在以对映异构体纯形式存在的手性胺碱的存在下，在惰性溶剂中，通过中间体对映体纯盐级转化成对映异构体纯的二羧酸单酯，将这些二羧酸单酯通过与叠氮化物反应在Curtius重排的意义上中间转化成相应的叠氮化物，随后转化为相应的重排的异氰酸酯，然后异氰酸酯与烯丙醇反应，得到通式（Ⅶ），最后是通式（Ⅳ）的环戊烷-β-氨基酸 I）通过分解氨基甲酸酯和酯官能团获得。

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