Stereoselective Preparation of (1S, 2R)- and (1S, 2S)-2-Hydroxy-7, 7-dimethylbicyclo[2.2.1]heptane-1-carboxylic Acids
Stereoselective Preparation of (1S, 2R)- and (1S, 2S)-2-Hydroxy-7, 7-dimethylbicyclo[2.2.1]heptane-1-carboxylic Acids
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(1S,2R)-和(1S,2S)-2-羟基-7,7-二甲基双环[2.2.1]庚烷-1-羧酸的立体选择性制备
DOI：
10.1248/cpb.38.1717
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发表时间：
1990
影响因子：
1.7
通讯作者：
T. Kunieda
中科院分区：
文献类型：
--
作者：
T. Ishizuka;K. Kimura;S. Ishibuchi;T. Kunieda
从(1S)-酮酸（7,7 -二甲基-2-氧-双环庚烷[2.2.1]-1-羧酸）开始，实现了简单的高收率非对映纯(1S, 2R)-和(1S, 2S)-2-羟基- 7,7 -二甲基-双环庚烷[2.2.1]-1-羧酸的合成，具有潜在的手性助剂作用。后者（2-内异构体）的关键步骤包括碱催化的(1S, 2R)-2-羟基异构体（2-外异构体）的外映，完全由L-Selectride[〇！还原醛醇反应还原烷基酮酸酯。
Starting with (1S)-ketopinic acid (7, 7-dimethyl-2-oxo-bicyclo[2.2.1]heptane-1-carboxylic acid), a facile high-yield synthesis of diastereomerically pure (1S, 2R)- and (1S, 2S)-2-hydroxy-7, 7-dimethylbicyclo[2.2.1]heptane-1-carboxylic acids, potentially useful as chiral auxiliaries, has been achieved : the key step for the latter (2-endo isomer) involves the base-catalyzed epimerization of the (1S, 2R)-2-hydoxy isomer (2-exo-isomer), exclusively formed by the L-Selectride[○!R] reduction of alkyl ketopinate, via the retro-aldol reaction.