A highly regio- and diastereoselective TiCl4-mediated vinylogous Mukaiyama aldol reaction using the chiral vinylketene silyl N,O-acetal has been developed. The present vinylogous Mukaiyama aldol reaction provides a unique and effective means of controlling remote asymmetric induction. The methyl group at the α-position is important in achieving a high level of stereoselectivity. From a synthetic point of view, this methodology can provide a one-step construction of δ-hydroxy-α,γ-dimethyl-α,β-unsaturated carbonyl unit that is seen in many natural polyketide products.
ASJC Scopus subject areas
- Colloid and Surface Chemistry