Enantioselective imidazole-directed allylation of aldimines and ketimines.
A new chiral allylchlorosilane has been developed that allows the highly enantioselective allylation and crotylation of a range of 2-imidazolylaldimines and ketimines. The method may be exploited for the protecting group-free synthesis of a diverse array of imidazole-bearing chiral carbinamines and, when coupled with ring-closing metathesis reactions, allows the one-pot synthesis of unusual heterocyclic motifs with potential relevance in medicinal chemistry.
Perl
Nicholas R
NR
Department of Chemistry, Columbia University, New York, New York 10027, USA.
Leighton
James L
JL
D000447:Aldehydes / Q000737:chemistry*; D000498:Allyl Compounds / Q000737:chemistry*; D002626:Chemistry, Pharmaceutical; D007093:Imidazoles / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D012821:Silanes / Q000737:chemistry*; D013237:Stereoisomerism
D000447:Aldehydes; D000498:Allyl Compounds; D007093:Imidazoles; D007097:Imines; D007659:Ketones; D012821:Silanes; C524028:allylchlorosilane