Diastereoselective conjugate addition of thiols to camphor pyrazolidinone derived chiral α,β-unsaturated carbonyls: Synthesis of β-mercaptocarboxylic acid derivatives

C. H. Lin; K. S. Yang; J. F. Pan; K. Chen

doi:10.1016/S0040-4039(00)01157-6

Diastereoselective conjugate addition of thiols to camphor pyrazolidinone derived chiral α,β-unsaturated carbonyls: Synthesis of β-mercaptocarboxylic acid derivatives

C. H. Lin
, K. S. Yang
, J. F. Pan
, K. Chen^*

^*Corresponding author for this work

Department of Chemistry

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

34 Citations (Scopus)

Abstract

Reaction of chiral α,β-unsaturated carboxylic acid derivatives 2a-e derived from camphor pyrazolidinone 1 with thiols affords β-mercaptocarboxylic acid derivatives 3a-e with a wide range of stereoselectivities (up to > 90% de). The stereoselectivity as a function of Lewis acid is described. The auxiliary can be easily recovered from the Michael adducts under mild conditions. (C) 2000 Elsevier Science Ltd.

Original language	English
Pages (from-to)	6815-6819
Number of pages	5
Journal	Tetrahedron Letters
Volume	41
Issue number	35
DOIs	https://doi.org/10.1016/S0040-4039(00)01157-6
Publication status	Published - 2000 Aug 26

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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@article{a27db83f329844d186d240facd8cd519,

title = "Diastereoselective conjugate addition of thiols to camphor pyrazolidinone derived chiral α,β-unsaturated carbonyls: Synthesis of β-mercaptocarboxylic acid derivatives",

abstract = "Reaction of chiral α,β-unsaturated carboxylic acid derivatives 2a-e derived from camphor pyrazolidinone 1 with thiols affords β-mercaptocarboxylic acid derivatives 3a-e with a wide range of stereoselectivities (up to > 90\% de). The stereoselectivity as a function of Lewis acid is described. The auxiliary can be easily recovered from the Michael adducts under mild conditions. (C) 2000 Elsevier Science Ltd.",

author = "Lin, \{C. H.\} and Yang, \{K. S.\} and Pan, \{J. F.\} and K. Chen",

note = "Funding Information: Financial support by the National Science Council of the Republic of China and the collection and processing of the X-ray data for 2b – c , 2e , 3a (R 3 =CH 2 CH 2 CO 2 Me) and 3e (R 1 =β-Me, R 3 =COPh) by Professor C.-H. Ueng (National Taiwan Normal University) and the Taipei Instrumentation Center, College of Science (National Taiwan University), are gratefully acknowledged. ",

year = "2000",

month = aug,

day = "26",

doi = "10.1016/S0040-4039(00)01157-6",

language = "English",

volume = "41",

pages = "6815--6819",

journal = "Tetrahedron Letters",

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TY - JOUR

T1 - Diastereoselective conjugate addition of thiols to camphor pyrazolidinone derived chiral α,β-unsaturated carbonyls

T2 - Synthesis of β-mercaptocarboxylic acid derivatives

AU - Lin, C. H.

AU - Yang, K. S.

AU - Pan, J. F.

AU - Chen, K.

N1 - Funding Information: Financial support by the National Science Council of the Republic of China and the collection and processing of the X-ray data for 2b – c , 2e , 3a (R 3 =CH 2 CH 2 CO 2 Me) and 3e (R 1 =β-Me, R 3 =COPh) by Professor C.-H. Ueng (National Taiwan Normal University) and the Taipei Instrumentation Center, College of Science (National Taiwan University), are gratefully acknowledged.

PY - 2000/8/26

Y1 - 2000/8/26

N2 - Reaction of chiral α,β-unsaturated carboxylic acid derivatives 2a-e derived from camphor pyrazolidinone 1 with thiols affords β-mercaptocarboxylic acid derivatives 3a-e with a wide range of stereoselectivities (up to > 90% de). The stereoselectivity as a function of Lewis acid is described. The auxiliary can be easily recovered from the Michael adducts under mild conditions. (C) 2000 Elsevier Science Ltd.

AB - Reaction of chiral α,β-unsaturated carboxylic acid derivatives 2a-e derived from camphor pyrazolidinone 1 with thiols affords β-mercaptocarboxylic acid derivatives 3a-e with a wide range of stereoselectivities (up to > 90% de). The stereoselectivity as a function of Lewis acid is described. The auxiliary can be easily recovered from the Michael adducts under mild conditions. (C) 2000 Elsevier Science Ltd.

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U2 - 10.1016/S0040-4039(00)01157-6

DO - 10.1016/S0040-4039(00)01157-6

M3 - Article

AN - SCOPUS:0034718324

SN - 0040-4039

VL - 41

SP - 6815

EP - 6819

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 35

ER -

Diastereoselective conjugate addition of thiols to camphor pyrazolidinone derived chiral α,β-unsaturated carbonyls: Synthesis of β-mercaptocarboxylic acid derivatives

Abstract

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