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Catalytic Asymmetric Addition of Organolithium Reagents to Aldehydes
Author(s) -
Veguillas Marcos,
Solà Ricard,
Shaw Luke,
Maciá Beatriz
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201600104
Subject(s) - methyllithium , chemistry , reagent , enantioselective synthesis , catalysis , alkylation , organic chemistry , aldehyde , titanium , combinatorial chemistry , organolithium compounds , ion , deprotonation
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.