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

Highly diastereo- and enantioselective catalytic domino thia-Michael/aldol reactions: synthesis of benzothiopyrans with three contiguous stereocenters
Highly diastereo- and enantioselective catalytic domino thia-Michael/aldol reactions: synthesis of benzothiopyrans with three contiguous stereocenters
Highly enantioselective organocatalytic domino thia-Michael/aldol reactions between 2-mercaptoacetophenone and ?,?-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.
asymmetric catalysis, benzothiopyrans, domino reactions, thia-michael reaction, ?, ?-unsaturated aldehydes
1615-4150
237-242
Zhao, Gui-Ling
106737c0-2aeb-4805-a8d7-496b1ce04322
Vesely, Jan
1853ff19-a906-4321-bd69-f7e434176fc3
Rios, Ramon
609bedf2-e886-4d62-a676-a32b6f8c1441
Ibrahem, Ismail
3cbac9c1-431b-4a1f-8c41-92aa617254b0
Sundén, Henrik
fe114b08-1de1-4e88-9778-a9cddf3aa76d
Córdova, Armando
d2a1239f-708d-4f9c-bf7c-c095e9a27cac
Zhao, Gui-Ling
106737c0-2aeb-4805-a8d7-496b1ce04322
Vesely, Jan
1853ff19-a906-4321-bd69-f7e434176fc3
Rios, Ramon
609bedf2-e886-4d62-a676-a32b6f8c1441
Ibrahem, Ismail
3cbac9c1-431b-4a1f-8c41-92aa617254b0
Sundén, Henrik
fe114b08-1de1-4e88-9778-a9cddf3aa76d
Córdova, Armando
d2a1239f-708d-4f9c-bf7c-c095e9a27cac

Zhao, Gui-Ling, Vesely, Jan, Rios, Ramon, Ibrahem, Ismail, Sundén, Henrik and Córdova, Armando (2008) Highly diastereo- and enantioselective catalytic domino thia-Michael/aldol reactions: synthesis of benzothiopyrans with three contiguous stereocenters. Advanced Synthesis & Catalysis, 350 (2), 237-242. (doi:10.1002/adsc.200700407).

Record type: Article

Abstract

Highly enantioselective organocatalytic domino thia-Michael/aldol reactions between 2-mercaptoacetophenone and ?,?-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.

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More information

e-pub ahead of print date: 7 January 2008
Published date: 25 January 2008
Keywords: asymmetric catalysis, benzothiopyrans, domino reactions, thia-michael reaction, ?, ?-unsaturated aldehydes
Organisations: Chemistry

Identifiers

Local EPrints ID: 347747
URI: http://eprints.soton.ac.uk/id/eprint/347747
ISSN: 1615-4150
PURE UUID: 52bd4e20-e3bd-49bf-8a3e-3d5c89b114a2
ORCID for Ramon Rios: ORCID iD orcid.org/0000-0002-3843-8521

Catalogue record

Date deposited: 29 Jan 2013 14:23
Last modified: 03 Dec 2019 01:38

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