Tether-directed synthesis of highly substituted oxasilacycles via an intramolecular allylation employing allylsilanes.

ABSTRACT:

Background

Using a silyl tether to unite an aldehyde electrophile and allylsilane nucleophile into a single molecule allows a subsequent Lewis-acid-mediated allylation to proceed in an intramolecular sense and therefore receive all the benefits associated with such processes. However, with the ability to cleave the tether post allylation, a product that is the result of a net intermolecular reaction can be obtained. In the present study, four diastereoisomeric beta-silyloxy-alpha-methyl aldehydes, which contain an allylsilane tethered through the beta-carbinol centre, have been prepared, in order to probe how the relative configuration of the two stereogenic centres affects the efficiency and selectivity of the intramolecular allylation.

Results

Syn-aldehydes, syn-4a and syn

SUBMITTER: Jervis PJ 

PROVIDER: S-EPMC1810303 | biostudies-literature | 2007 Feb

REPOSITORIES: biostudies-literature