使用手性N-(2-羟甲基-4-吡咯烷基)苯甲酰胺模板对2-蒽甲酸进行对映体选择性光环二聚反应。

Enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylic acid using a chiral N-(2-hydroxymethyl-4- pyrrolidinyl)benzamide template.

作者信息

Mizoguchi Jun-ichi, Kawanami Yuko, Wada Takehiko, Kodama Kazuya, Anzai Kinsei, Yanagi Toshiharu, Inoue Yoshihisa

机构信息

Bio/Fine Chemicals Department, Nagase ChemteX Corporation, 2-2-3 Murotani, Nishi-ku, Kobe 651-2241, Japan.

出版信息

Org Lett. 2006 Dec 21;8(26):6051-4. doi: 10.1021/ol062501g.

DOI:10.1021/ol062501g

PMID:17165927

Abstract

[Structure: see text] Supramolecular enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylic acid (AC) was performed in the presence of (2S,4S)-4-amino-5-chloro-2-methoxy-N-(1-ethyl-2-hydroxymethyl-4-pyrrolidinyl)benzamide (TKS159), and its stereoisomers were employed as chiral templates. The TKS template provides us with a novel hydrogen-bonding and shielding motif for enantioface-selectively binding an AC molecule. Chiral products 2 and 3 were obtained in good enantiomeric excesses (ee's) of 40% and 40%, respectively.

摘要

[结构：见正文] 在(2S,4S)-4-氨基-5-氯-2-甲氧基-N-(1-乙基-2-羟甲基-4-吡咯烷基)苯甲酰胺(TKS159)存在下进行了2-蒽甲酸(AC)的超分子对映体选择性光环二聚反应，并将其立体异构体用作手性模板。TKS模板为对映面选择性结合AC分子提供了一种新颖的氢键和屏蔽基序。分别以40%和40%的良好对映体过量(ee值)获得了手性产物2和3。