Novel camphor-derived chiral auxiliaries: Significant solvent and additive effects on asymmetric reduction of chiral α-keto esters

Ying Yuan Chu, Chia Sheng Yu, Chiou Juy Chen, Kung Shuo Yang, Jung Chaing Lain, Chun Hui Lin, Kwunmin Chen

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Abstract

Stereoselective reduction of various α-keto esters 5a-d derived from exo-10,10-diphenyl-2,10-camphanediol 4a and exo-10,10-diphenyl-10-methoxy-2- camphanol 4b is described. High to excellent diastereomeric excess (99% de) with good chemical yields is obtained. The sense of stereoselectivity as a function of C10 modification is remarkable. Further, in the case of 5d, both diastereomers of α-hydroxyl esters can be obtained with excellent optical purity by the appropriate choice of reaction conditions. The influence of the solvents and additives on the reaction course has been investigated.

Original languageEnglish
Pages (from-to)6993-6998
Number of pages6
JournalJournal of Organic Chemistry
Volume64
Issue number19
DOIs
Publication statusPublished - 1999 Sep 17

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ASJC Scopus subject areas

  • Organic Chemistry

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