Open AccessSmI2-Mediated Radical Cyclizations Directed by a C−Si Bond
Author(s) -
Hassan Y. Harb,
Karl D. Collins,
J.V.G. Altur,
Sue Bowker,
Leonie Campbell,
David J. Procter
Publication year - 2010
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/ol102278c
Subject(s) - chemistry , bond , stereochemistry , medicinal chemistry , computational chemistry , business , finance
The use of a silicon stereocontrol element in cyclobutanol and cyclopentanol-forming cyclizations mediated by SmI(2) results in excellent diastereocontrol. The C-Si bond in the products of cyclization provides a versatile handle for further manipulation. An asymmetric route to cyclization substrates involving copper-catalyzed silyl transfer has also been developed.
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