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Tandem Michael/Michael reactions mediated by phosphines or aryl thiolates

Tandem Michael/Michael reactions mediated by phosphines or aryl thiolates
Tandem Michael/Michael reactions mediated by phosphines or aryl thiolates
Tri-n-butyl phosphine was found to effect tandem Michael/Michael cyclisations leading to the formation of cyclopentenes and cyclohexenes in good yields, whilst p-TolSH in conjunction with a catalytic amount of p-TolSNa effected cyclisation to the corresponding cyclopentanes and cyclohexanes.
phosphines, cyclizations, tandem reactions, aldol reactions, baylis-hillman-reaction, asymmetric-synthesis, michael additions, secondary-amines, conjugate addition, nucleophile, cycloalkenes, nitrogen, bis-enones
0040-4020
1100-1106
Brown, Paul M.
2b2dba2e-50be-4798-add3-4555bfd630ff
Käppel, Nina
b3c714f8-5e10-42af-8c85-47c4a16e0823
Murphy, Patrick J.
5ab567ae-c42c-44d4-8ae4-8b376cf2e6e6
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Hursthouse, Michael B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
Brown, Paul M.
2b2dba2e-50be-4798-add3-4555bfd630ff
Käppel, Nina
b3c714f8-5e10-42af-8c85-47c4a16e0823
Murphy, Patrick J.
5ab567ae-c42c-44d4-8ae4-8b376cf2e6e6
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Hursthouse, Michael B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da

Brown, Paul M., Käppel, Nina, Murphy, Patrick J., Coles, Simon J. and Hursthouse, Michael B. (2007) Tandem Michael/Michael reactions mediated by phosphines or aryl thiolates. Tetrahedron, 63 (5), 1100-1106. (doi:10.1016/j.tet.2006.11.064).

Record type: Article

Abstract

Tri-n-butyl phosphine was found to effect tandem Michael/Michael cyclisations leading to the formation of cyclopentenes and cyclohexenes in good yields, whilst p-TolSH in conjunction with a catalytic amount of p-TolSNa effected cyclisation to the corresponding cyclopentanes and cyclohexanes.

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More information

Published date: 29 January 2007
Keywords: phosphines, cyclizations, tandem reactions, aldol reactions, baylis-hillman-reaction, asymmetric-synthesis, michael additions, secondary-amines, conjugate addition, nucleophile, cycloalkenes, nitrogen, bis-enones

Identifiers

Local EPrints ID: 54257
URI: https://eprints.soton.ac.uk/id/eprint/54257
ISSN: 0040-4020
PURE UUID: 87e3a30f-c74e-4b63-9a6c-80a222012ab2
ORCID for Simon J. Coles: ORCID iD orcid.org/0000-0001-8414-9272

Catalogue record

Date deposited: 31 Jul 2008
Last modified: 14 Mar 2019 01:48

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