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.

SUBMITTER: Reznik SK 

PROVIDER: S-EPMC4142647 | biostudies-literature | 2012 Nov

REPOSITORIES: biostudies-literature