One-pot ring-closing metathesis-alkene cross metathesis reactions of sulfamide-linked enynes
One-pot ring-closing metathesis-alkene cross metathesis reactions of sulfamide-linked enynes
Ring-closing metathesis (RCM) of sulfamide-linked enynes 7, 11 and 12 containing disubstituted alkynes afforded a series of novel 7-membered cyclic sulfamides 13-15 in good yield. Substrates 5, 9 and 10 containing mono-substituted dlkynes gave either simple RCM products 18a-c or those arising from combinations of enyne RCM and olefin cross metathesis 16/17a-c depending on the reaction conditions. Not-ably, in the presence of two equivalents of styrene or ethyl acrylate, substrates 5, 9 and 10 containing terminal alkynes underwent selective enyne-RCM-olefin-cross metathesis to provide cyclic sulfamides 17a-c and 19b,c in yields of 54-83%.
sulfamides, enynes, domino reactions, dienes, metathesis cyclic sulfonamides, strategies
800-806
Salim, Sofia S.
d5de5263-b418-469b-b3f5-bdd05ee48387
Bellingham, Richard K.
ffa421f3-f2fb-4de9-b3f1-bba3f18b8976
Brown, Richard C.D.
21ce697a-7c3a-480e-919f-429a3d8550f5
13 February 2004
Salim, Sofia S.
d5de5263-b418-469b-b3f5-bdd05ee48387
Bellingham, Richard K.
ffa421f3-f2fb-4de9-b3f1-bba3f18b8976
Brown, Richard C.D.
21ce697a-7c3a-480e-919f-429a3d8550f5
Salim, Sofia S., Bellingham, Richard K. and Brown, Richard C.D.
(2004)
One-pot ring-closing metathesis-alkene cross metathesis reactions of sulfamide-linked enynes.
European Journal of Organic Chemistry, (4), .
(doi:10.1002/ejoc.200300725).
Abstract
Ring-closing metathesis (RCM) of sulfamide-linked enynes 7, 11 and 12 containing disubstituted alkynes afforded a series of novel 7-membered cyclic sulfamides 13-15 in good yield. Substrates 5, 9 and 10 containing mono-substituted dlkynes gave either simple RCM products 18a-c or those arising from combinations of enyne RCM and olefin cross metathesis 16/17a-c depending on the reaction conditions. Not-ably, in the presence of two equivalents of styrene or ethyl acrylate, substrates 5, 9 and 10 containing terminal alkynes underwent selective enyne-RCM-olefin-cross metathesis to provide cyclic sulfamides 17a-c and 19b,c in yields of 54-83%.
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Published date: 13 February 2004
Keywords:
sulfamides, enynes, domino reactions, dienes, metathesis cyclic sulfonamides, strategies
Identifiers
Local EPrints ID: 20315
URI: http://eprints.soton.ac.uk/id/eprint/20315
ISSN: 1434-193X
PURE UUID: 5187ec29-3a60-45cd-a042-38a84c262488
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Date deposited: 17 Feb 2006
Last modified: 16 Mar 2024 02:54
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Author:
Sofia S. Salim
Author:
Richard K. Bellingham
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