Hosomi-Sakurai reactions of silacyclohexenes.
Silacyclic allyl silanes, derived from silene-diene Diels-Alder reactions, combine with acetals in the presence of Lewis acids to afford, following oxidation of the intermediate fluorosilane, either butane-1,4-diols or tetrahydronaphthalenes containing four contiguous chiral centres with moderate to good diastereoselectivity.
Hughes
Nicholas J
NJ
Department of Chemistry, University of Durham, Science Laboratories, South Road, Durham DH1 3LE, UK.
Pullin
Robert D C
RD
Sanganee
Mahesh J
MJ
Sellars
Jonathan D
JD
Steel
Patrick G
PG
Turner
Michael J
MJ
D000080:Acetals / Q000737:chemistry; D018360:Crystallography, X-Ray; D053138:Cyclohexenes / Q000138:chemical synthesis / Q000737:chemistry*; D005459:Fluorides / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D015394:Molecular Structure; D012828:Silicones / Q000737:chemistry*
D000080:Acetals; D053138:Cyclohexenes; D012828:Silicones; D005459:Fluorides