Axial Chirality by Asymmetric Induction. Diastereomeric Allene Formation via Silicon as a Chiral Auxiliary

Article abstract of DOI:10.1021/jo00269a002

Interaction of alkenylidenecarbenes, RCH=C=C:, R = CH3 and t-Bu, with chiral α-NpPhMeSi^*H results in chiral allenes with a 3.5 +/- 0.5percent and 10.5 +/- 0.5percent diastereomeric excess, respectively.Hence the transfer of central chirality to axial chirality, via silicon as a chiral auxiliary, has been established.These results are discussed, and a transmission state is proposed.