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Assessing the scope of the tandem Michael/intramolecular aldol reaction mediated by secondary amines, thiols and phosphines

Assessing the scope of the tandem Michael/intramolecular aldol reaction mediated by secondary amines, thiols and phosphines
Assessing the scope of the tandem Michael/intramolecular aldol reaction mediated by secondary amines, thiols and phosphines
The outcome of a tandem Michael/intramolecular aldol reaction which is mediated by secondary amines, thiols and phosphines has been found to be highly substrate dependent, with the best results being obtained for the formation of 5 and 6-membered rings using thiol or thiolate nucleophiles. Amine and phosphine mediated cyclisations were found to be problematic in several cases but were still effective methods for the formation of 5-7 membered rings.
tandem michael/intramolecular aldol reaction, secondary amine, thiols, phosphinesalpha, beta-unsaturated carbonyl compound, 1-acylethenyl anionequivalent, baylis-hillman-reaction, asymmetric-synthesis, michael-aldol, esters, 1, 4-addition, model, route
0040-4020
7771-7784
Richards, E. L.
0c2f4b5c-5117-448f-a026-d884b3fc8990
Murphy, P. J.
e361583b-6b55-4418-a536-24f3405273a2
Dinon, F.
d34df6f8-dc10-4f3e-89b1-aa689149a7bb
Fratucello, S.
4726c0dd-ab31-4f91-b335-9ba5584b5d74
Brown, P. M.
b785f4b3-4544-497a-bc51-11eb525615db
Gelbrich, T.
42309d69-eaf1-4bb7-ba2e-db61f338e370
Hursthouse, M. B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
Richards, E. L.
0c2f4b5c-5117-448f-a026-d884b3fc8990
Murphy, P. J.
e361583b-6b55-4418-a536-24f3405273a2
Dinon, F.
d34df6f8-dc10-4f3e-89b1-aa689149a7bb
Fratucello, S.
4726c0dd-ab31-4f91-b335-9ba5584b5d74
Brown, P. M.
b785f4b3-4544-497a-bc51-11eb525615db
Gelbrich, T.
42309d69-eaf1-4bb7-ba2e-db61f338e370
Hursthouse, M. B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da

Richards, E. L., Murphy, P. J., Dinon, F., Fratucello, S., Brown, P. M., Gelbrich, T. and Hursthouse, M. B. (2001) Assessing the scope of the tandem Michael/intramolecular aldol reaction mediated by secondary amines, thiols and phosphines. Tetrahedron, 57 (36), 7771-7784. (doi:10.1016/S0040-4020(01)00744-X).

Record type: Article

Abstract

The outcome of a tandem Michael/intramolecular aldol reaction which is mediated by secondary amines, thiols and phosphines has been found to be highly substrate dependent, with the best results being obtained for the formation of 5 and 6-membered rings using thiol or thiolate nucleophiles. Amine and phosphine mediated cyclisations were found to be problematic in several cases but were still effective methods for the formation of 5-7 membered rings.

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More information

Published date: 3 September 2001
Keywords: tandem michael/intramolecular aldol reaction, secondary amine, thiols, phosphinesalpha, beta-unsaturated carbonyl compound, 1-acylethenyl anionequivalent, baylis-hillman-reaction, asymmetric-synthesis, michael-aldol, esters, 1, 4-addition, model, route

Identifiers

Local EPrints ID: 19610
URI: http://eprints.soton.ac.uk/id/eprint/19610
ISSN: 0040-4020
PURE UUID: 64fb2e66-4f2b-40b5-84c3-c8d9861d418e

Catalogue record

Date deposited: 14 Feb 2006
Last modified: 15 Jul 2019 19:26

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