Exo-10,10-diphenyl-2,10-camphanediol as a new chiral auxiliary in asymmetric reduction

C. J. Chen; Y. Y. Chu; Y. Y. Liao; Z. H. Tsai; C. C. Wang; K. Chen

doi:10.1016/S0040-4039(98)02548-9

Exo-10,10-diphenyl-2,10-camphanediol as a new chiral auxiliary in asymmetric reduction

C. J. Chen, Y. Y. Chu, Y. Y. Liao, Z. H. Tsai, C. C. Wang, K. Chen^*

^*Corresponding author for this work

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

13 Citations (Scopus)

Abstract

Stereoselective reduction of α-keto ester derived from exo-10,10- diphenyl-2,10-camphanediol with various hydrides proceeded with high diastereoselectivities (≥ 96% de) to afford the corresponding α-hydroxy ester with excellent yields. Change of reducing reagents and molar ratio modifications leading to dramatic changes in diastereofacial selectivity were examined. The auxiliary can be recovered from the asymmetric reaction products without loss of chirality.

Original language	English
Pages (from-to)	1141-1144
Number of pages	4
Journal	Tetrahedron Letters
Volume	40
Issue number	6
DOIs	https://doi.org/10.1016/S0040-4039(98)02548-9
Publication status	Published - 1999 Feb 5
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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abstract = "Stereoselective reduction of α-keto ester derived from exo-10,10- diphenyl-2,10-camphanediol with various hydrides proceeded with high diastereoselectivities (≥ 96% de) to afford the corresponding α-hydroxy ester with excellent yields. Change of reducing reagents and molar ratio modifications leading to dramatic changes in diastereofacial selectivity were examined. The auxiliary can be recovered from the asymmetric reaction products without loss of chirality.",

author = "Chen, {C. J.} and Chu, {Y. Y.} and Liao, {Y. Y.} and Tsai, {Z. H.} and Wang, {C. C.} and K. Chen",

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T1 - Exo-10,10-diphenyl-2,10-camphanediol as a new chiral auxiliary in asymmetric reduction

AU - Chen, C. J.

AU - Chu, Y. Y.

AU - Liao, Y. Y.

AU - Tsai, Z. H.

AU - Wang, C. C.

AU - Chen, K.

PY - 1999/2/5

Y1 - 1999/2/5

N2 - Stereoselective reduction of α-keto ester derived from exo-10,10- diphenyl-2,10-camphanediol with various hydrides proceeded with high diastereoselectivities (≥ 96% de) to afford the corresponding α-hydroxy ester with excellent yields. Change of reducing reagents and molar ratio modifications leading to dramatic changes in diastereofacial selectivity were examined. The auxiliary can be recovered from the asymmetric reaction products without loss of chirality.

AB - Stereoselective reduction of α-keto ester derived from exo-10,10- diphenyl-2,10-camphanediol with various hydrides proceeded with high diastereoselectivities (≥ 96% de) to afford the corresponding α-hydroxy ester with excellent yields. Change of reducing reagents and molar ratio modifications leading to dramatic changes in diastereofacial selectivity were examined. The auxiliary can be recovered from the asymmetric reaction products without loss of chirality.

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 6

ER -

Exo-10,10-diphenyl-2,10-camphanediol as a new chiral auxiliary in asymmetric reduction

Abstract

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