title: Diastereoselective synthesis of eight-membered-ring allenes from propargylic epoxides and aldehydes by silylene insertion into carbon-oxygen bonds.
abstract: Bent out of shape: Silver-catalyzed insertions of silylenes into propargylic CO bonds of epoxides regioselectively form 1,2-silaoxetanes, which add to aldehydes to give the title allenes as single diastereomers (see scheme; Ts=4-toluenesulfonyl). An X-ray crystal structure confirmed the stereochemistry of the allene, which is bent significantly from linearity (164°).
authors.affiliation: Department of Chemistry, New York University, 100 Washington Square East, New York, NY 10003 (USA).
authors.forename: Christina Z
authors.initials: CZ
authors.lastname: Rotsides
authors.forename: Chunhua
authors.initials: C
authors.lastname: Hu
authors.forename: K A
authors.initials: KA
authors.lastname: Woerpel
keywords: allenes; medium-ring compounds; reactive intermediates; silicon; strained molecules