SmI2-mediated radical cyclizations directed by a C-Si bond.
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.
School of Chemistry, University of Manchester, Oxford Road, Manchester, M13 9PL, United Kingdom.
Hassan Y
HY
Harb
Karl D
KD
Collins
Jose V
JV
Garcia Altur
Sue
S
Bowker
Leonie
L
Campbell
David J
DJ
Procter
D002244:Carbon / Q000737:chemistry*; D003500:Cyclization; D007454:Iodides / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D010084:Oxidation-Reduction; D012493:Samarium / Q000737:chemistry*; D012825:Silicon / Q000737:chemistry*; D013237:Stereoisomerism
D007454:Iodides; D012493:Samarium; D002244:Carbon; C409809:samarium diiodide; D012825:Silicon