Chiral relay: a novel strategy for the control and amplification of enantioselectivity in chiral Lewis acid promoted reactions.
Chiral Lewis acid catalysis has emerged as one of the premiere method to control stereochemistry. Much effort has gone into the design of superior ligands with increasing steric extension to shield distant reactive sites. We report here an alternative and complementary approach based on a "chiral relay". This strategy focuses on the improved design of achiral templates which may relay and amplify the stereochemistry from ligands. The essence of this strategy is that the chiral Lewis acid would effectively convert an achiral template into a chiral non-racemic template. This approach combines the advantages of enantioselective catalysis (substoichiometric amount of the chiral inducer) with the ones of chiral auxiliary control (efficient and predictable stereocontrol).
Corminboeuf
Olivier
O
University of Bern, Department of Chemistry and Biochemistry, Freiestrasse 3, 3000 Berne 9, Switzerland.
Quaranta
Laura
L
Renaud
Philippe
P
Liu
Mei
M
Jasperse
Craig P
CP
Sibi
Mukund P
MP
D000143:Acids / Q000737:chemistry*; D002625:Chemistry, Organic / Q000379:methods*; D008968:Molecular Conformation; D013237:Stereoisomerism; D013440:Sulfides / Q000737:chemistry; D013449:Sulfonamides / Q000737:chemistry
D000143:Acids; D013440:Sulfides; D013449:Sulfonamides