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Samarium diiodide coupling of enones: a remarkable cascade sequence

Samarium diiodide coupling of enones: a remarkable cascade sequence
Samarium diiodide coupling of enones: a remarkable cascade sequence
Treatment of cyclic enones with SmI2 in THF/MeOH (4:1) led to tricyclic diol products in one step and, in the case of enone 7, gave the tetracycle 13 as a single diastereoisomer in up to 67% yield.
mechanistic insights, carbonyl-compounds, iodide, reduction, hydrodimerization, cyclizations, halides
1523-7060
1943-1945
Howells, Dean M.
e91b7f3d-ed6b-4f43-8ab4-c98dc86ef9c7
Barker, Sarah M.
d4c8400a-eeff-45d8-8ce8-cb28746d2d25
Watson, Faye C.
e00d8ed6-beb8-47a7-ae99-90519ecdf7a4
Light, Mark E.
cf57314e-6856-491b-a8d2-2dffc452e161
Hursthouse, Michael B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
Kilburn, Jeremy D.
e64ded70-825a-40ec-816b-c4605e007e7a
Howells, Dean M.
e91b7f3d-ed6b-4f43-8ab4-c98dc86ef9c7
Barker, Sarah M.
d4c8400a-eeff-45d8-8ce8-cb28746d2d25
Watson, Faye C.
e00d8ed6-beb8-47a7-ae99-90519ecdf7a4
Light, Mark E.
cf57314e-6856-491b-a8d2-2dffc452e161
Hursthouse, Michael B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
Kilburn, Jeremy D.
e64ded70-825a-40ec-816b-c4605e007e7a

Howells, Dean M., Barker, Sarah M., Watson, Faye C., Light, Mark E., Hursthouse, Michael B. and Kilburn, Jeremy D. (2004) Samarium diiodide coupling of enones: a remarkable cascade sequence. Organic Letters, 6 (12), 1943-1945. (doi:10.1021/ol049563w).

Record type: Article

Abstract

Treatment of cyclic enones with SmI2 in THF/MeOH (4:1) led to tricyclic diol products in one step and, in the case of enone 7, gave the tetracycle 13 as a single diastereoisomer in up to 67% yield.

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More information

Published date: 10 June 2004
Keywords: mechanistic insights, carbonyl-compounds, iodide, reduction, hydrodimerization, cyclizations, halides

Identifiers

Local EPrints ID: 20238
URI: http://eprints.soton.ac.uk/id/eprint/20238
ISSN: 1523-7060
PURE UUID: 3a3a9512-d82a-4f4c-a8d8-7e9424bc8a7e
ORCID for Mark E. Light: ORCID iD orcid.org/0000-0002-0585-0843

Catalogue record

Date deposited: 20 Feb 2006
Last modified: 16 Mar 2024 03:04

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Contributors

Author: Dean M. Howells
Author: Sarah M. Barker
Author: Faye C. Watson
Author: Mark E. Light ORCID iD
Author: Jeremy D. Kilburn

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