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

doi:10.1021/jo9902188

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^*

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

42 Citations (Scopus)

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 language	English
Pages (from-to)	6993-6998
Number of pages	6
Journal	Journal of Organic Chemistry
Volume	64
Issue number	19
DOIs	https://doi.org/10.1021/jo9902188
Publication status	Published - 1999 Sept 17

ASJC Scopus subject areas

Organic Chemistry

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10.1021/jo9902188

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

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.",

author = "Chu, {Ying Yuan} and Yu, {Chia Sheng} and Chen, {Chiou Juy} and Yang, {Kung Shuo} and Lain, {Jung Chaing} and Lin, {Chun Hui} and Kwunmin Chen",

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T1 - Novel camphor-derived chiral auxiliaries

T2 - Significant solvent and additive effects on asymmetric reduction of chiral α-keto esters

AU - Chu, Ying Yuan

AU - Yu, Chia Sheng

AU - Chen, Chiou Juy

AU - Yang, Kung Shuo

AU - Lain, Jung Chaing

AU - Lin, Chun Hui

AU - Chen, Kwunmin

PY - 1999/9/17

Y1 - 1999/9/17

N2 - 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.

AB - 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.

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

Abstract

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