title: Complex fragment coupling by crotylation: A powerful tool for polyketide natural product synthesis.
abstract: The first examples of the use of crotylation as a stereocontrolled complex fragment coupling strategy are described. Asymmetric aldehyde isoprenylation provides access to 2-substituted-1,3-butadienes that may be subjected to highly regio- and stereoselective 1,4 hydrosilylation with trichlorosilane. After complexation with a chiral diamine, the 2-sub-stituted-cis-crotylsilanes may be employed in highly diastereoselective Sc(OTf)3-catalyzed aldehdye crotylation reactions.
authors.affiliation: Department of Chemistry, Columbia University, 3000 Broadway, New York, New York, 10027, USA. ; Tel: (+1) 212-854-4262.
authors.forename: Samuel K
authors.initials: SK
authors.lastname: Reznik
authors.affiliation: Department of Chemistry, Columbia University, 3000 Broadway, New York, New York, 10027, USA. ; Tel: (+1) 212-854-4262.
authors.forename: Brian S
authors.initials: BS
authors.lastname: Marcus
authors.affiliation: Department of Chemistry, Columbia University, 3000 Broadway, New York, New York, 10027, USA. ; Tel: (+1) 212-854-4262.
authors.forename: James L
authors.initials: JL
authors.lastname: Leighton