Catalytic Asymmetric Addition of Organolithium Reagents to Aldehydes.

Veguillas, Marcos; Solà, Ricard; Shaw, Luke; Maciá, Beatriz

Herein we report an efficient catalytic system for the titanium-promoted enantioselective addition of organolithium reagents to aldehydes, based on chiral Ar-BINMOL ligands. Unprecedented yields and enantioselectivities are achieved in the alkylation reactions of aliphatic aldehydes. Remarkably, methyllithium can be added to a wide variety of aromatic and aliphatic aldehydes, providing versatile chiral methyl carbinol units in a simple one-pot procedure under mild conditions and in very short reaction times.

ORGANOLITHIUM compounds; ALDEHYDES; TITANIUM catalysts; CATALYSIS; ALKYLATION; METHYLLITHIUM

European Journal of Organic Chemistry, 2016, Vol 2016, Issue 9, p1788

1434-193X

Academic Journal

10.1002/ejoc.201600104