One-pot enyne ring-closing metathesis–Diels–Alder reactions for the synthesis of polycyclic sulfamides
One-pot enyne ring-closing metathesis–Diels–Alder reactions for the synthesis of polycyclic sulfamides
Ring-closing metathesis (RCM) and sequential Yb(OTf)3 promoted Diels–Alder reactions of sulfamide-linked enynes proceeded selectively in one-pot to afford a series of bicyclic and tricyclic sulfamides. Excellent levels of diastereoselectivity are observed for the cycloaddition step, with only the endo-adducts being isolated. The protocol was further extended to incorporate a one-pot RCM–cross metathesis (CM)–Diels–Alder sequence, permitting rapid access to high levels of molecular complexity from simple and easily accessible precursors.
metathesis, enyne, sulfamide, diels–alder, One-pot
3700-3706
Hill-Cousins, Joseph T.
3fd2a389-1612-4d9d-8322-afcc0c401ada
Salim, Sofia S.
d5de5263-b418-469b-b3f5-bdd05ee48387
Bakar, Youssef M.
7ae25c22-cc87-42d5-9548-b070d216eb1a
Bellingham, Richard K.
ffa421f3-f2fb-4de9-b3f1-bba3f18b8976
Light, Mark E.
cf57314e-6856-491b-a8d2-2dffc452e161
Brown, Richard C.D.
21ce697a-7c3a-480e-919f-429a3d8550f5
10 June 2014
Hill-Cousins, Joseph T.
3fd2a389-1612-4d9d-8322-afcc0c401ada
Salim, Sofia S.
d5de5263-b418-469b-b3f5-bdd05ee48387
Bakar, Youssef M.
7ae25c22-cc87-42d5-9548-b070d216eb1a
Bellingham, Richard K.
ffa421f3-f2fb-4de9-b3f1-bba3f18b8976
Light, Mark E.
cf57314e-6856-491b-a8d2-2dffc452e161
Brown, Richard C.D.
21ce697a-7c3a-480e-919f-429a3d8550f5
Hill-Cousins, Joseph T., Salim, Sofia S., Bakar, Youssef M., Bellingham, Richard K., Light, Mark E. and Brown, Richard C.D.
(2014)
One-pot enyne ring-closing metathesis–Diels–Alder reactions for the synthesis of polycyclic sulfamides.
Tetrahedron, 70 (23), .
(doi:10.1016/j.tet.2014.04.014).
Abstract
Ring-closing metathesis (RCM) and sequential Yb(OTf)3 promoted Diels–Alder reactions of sulfamide-linked enynes proceeded selectively in one-pot to afford a series of bicyclic and tricyclic sulfamides. Excellent levels of diastereoselectivity are observed for the cycloaddition step, with only the endo-adducts being isolated. The protocol was further extended to incorporate a one-pot RCM–cross metathesis (CM)–Diels–Alder sequence, permitting rapid access to high levels of molecular complexity from simple and easily accessible precursors.
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More information
Accepted/In Press date: 7 April 2014
e-pub ahead of print date: 13 April 2014
Published date: 10 June 2014
Keywords:
metathesis, enyne, sulfamide, diels–alder, One-pot
Identifiers
Local EPrints ID: 385733
URI: http://eprints.soton.ac.uk/id/eprint/385733
ISSN: 0040-4020
PURE UUID: db0f5c78-3640-4ed9-b047-f1eb72ed8fde
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Date deposited: 21 Jan 2016 14:39
Last modified: 15 Mar 2024 03:01
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Contributors
Author:
Joseph T. Hill-Cousins
Author:
Sofia S. Salim
Author:
Youssef M. Bakar
Author:
Richard K. Bellingham
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