Asymmetric Grignard Synthesis of Tertiary Alcohols through Rational Ligand Design.
A simple, general and practical method is reported for highly enantioselective construction of tertiary alcohols through the direct addition of organomagnesium reagents to ketones. Discovered by rational ligand design based on a mechanistic hypothesis, it has an unprecedented broad scope. It utilizes a new type of chiral tridentate diamine/phenol ligand that is easily removed from the reaction mixture. It is exemplified by application to a formal asymmetric synthesis (>95:5 d.r.) of vitamin E.
Centre for Synthesis and Chemical Biology, School of Chemistry, University College Dublin, Belfield, Dublin, 4, Ireland.
Bartosz
0000-0002-9503-0792
B
Bieszczad
Centre for Synthesis and Chemical Biology, School of Chemistry, University College Dublin, Belfield, Dublin, 4, Ireland.
Declan G
0000-0002-1272-4423
DG
Gilheany
Grignard synthesis; asymmetric synthesis; tertiary alcohols; tridentate ligands; vitamin E