Highly diastereo- And enantioselective catalytic domino thia-Michael/aldol reactions: Synthesis of benzothiopyrans with three contiguous stereocenters

Gui Ling Zhao; Jan Veselý; Ramon Rios; Ismail Ibrahem; Henrik Sundén; Armando Córdova

doi:10.1002/adsc.200700407

Highly diastereo- And enantioselective catalytic domino thia-Michael/aldol reactions: Synthesis of benzothiopyrans with three contiguous stereocenters

Gui Ling Zhao
, Jan Veselý
, Ramon Rios
, Ismail Ibrahem
, Henrik Sundén
, Armando Córdova

Chemistry

Arrhenius Laboratory

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

71 Scopus citations

Abstract

Highly enantioselective organocatalytic domino thia-Michael/aldol reactions between 2-mercaptoacetophenone and α,β-unsaturated aldehydes are presented. The reactions proceed with excellent chemo-, diastereo- and enantioselectivity to give the corresponding benzothiopyran derivatives in high yields with up to > 15:1 dr and 96 to > 99% ee.

Original language	British English
Pages (from-to)	237-242
Number of pages	6
Journal	Advanced Synthesis and Catalysis
Volume	350
Issue number	2
DOIs	https://doi.org/10.1002/adsc.200700407
State	Published - Jan 2008

Keywords

α,β-Unsaturated Aldehydes
Asymmetric catalysis
Benzothiopyrans
Domino reactions
Thia-Michael reaction

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10.1002/adsc.200700407

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title = "Highly diastereo- And enantioselective catalytic domino thia-Michael/aldol reactions: Synthesis of benzothiopyrans with three contiguous stereocenters",

abstract = "Highly enantioselective organocatalytic domino thia-Michael/aldol reactions between 2-mercaptoacetophenone and α,β-unsaturated aldehydes are presented. The reactions proceed with excellent chemo-, diastereo- and enantioselectivity to give the corresponding benzothiopyran derivatives in high yields with up to > 15:1 dr and 96 to > 99\% ee.",

keywords = "α,β-Unsaturated Aldehydes, Asymmetric catalysis, Benzothiopyrans, Domino reactions, Thia-Michael reaction",

author = "Zhao, \{Gui Ling\} and Jan Vesel{\'y} and Ramon Rios and Ismail Ibrahem and Henrik Sund{\'e}n and Armando C{\'o}rdova",

year = "2008",

month = jan,

doi = "10.1002/adsc.200700407",

language = "British English",

volume = "350",

pages = "237--242",

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T1 - Highly diastereo- And enantioselective catalytic domino thia-Michael/aldol reactions

T2 - Synthesis of benzothiopyrans with three contiguous stereocenters

AU - Zhao, Gui Ling

AU - Veselý, Jan

AU - Rios, Ramon

AU - Ibrahem, Ismail

AU - Sundén, Henrik

AU - Córdova, Armando

PY - 2008/1

Y1 - 2008/1

N2 - Highly enantioselective organocatalytic domino thia-Michael/aldol reactions between 2-mercaptoacetophenone and α,β-unsaturated aldehydes are presented. The reactions proceed with excellent chemo-, diastereo- and enantioselectivity to give the corresponding benzothiopyran derivatives in high yields with up to > 15:1 dr and 96 to > 99% ee.

AB - Highly enantioselective organocatalytic domino thia-Michael/aldol reactions between 2-mercaptoacetophenone and α,β-unsaturated aldehydes are presented. The reactions proceed with excellent chemo-, diastereo- and enantioselectivity to give the corresponding benzothiopyran derivatives in high yields with up to > 15:1 dr and 96 to > 99% ee.

KW - α,β-Unsaturated Aldehydes

KW - Asymmetric catalysis

KW - Benzothiopyrans

KW - Domino reactions

KW - Thia-Michael reaction

UR - https://www.scopus.com/pages/publications/38849113311

U2 - 10.1002/adsc.200700407

DO - 10.1002/adsc.200700407

M3 - Article

AN - SCOPUS:38849113311

SN - 1615-4150

VL - 350

SP - 237

EP - 242

JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

IS - 2

ER -

Highly diastereo- And enantioselective catalytic domino thia-Michael/aldol reactions: Synthesis of benzothiopyrans with three contiguous stereocenters

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Keywords

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