General access to chiral N-alkyl terminal aziridines via organocatalysis.
A three step, one-pot protocol involving enantioselective alpha-chlorination of aldehydes, subsequent reductive amination with a primary amine, and S(N)2 displacement to afford chiral N-alkyl terminal aziridines in 40-65% yield (74-87%/step) and, in most cases, >90% ee is reported.
Fadeyi
Olugbeminiyi O
OO
Department of Chemistry, Vanderbilt Institute of Chemical Biology, Vanderbilt University Medical Center, Nashville, Tennessee 37232, USA.
Schulte
Michael L
ML
Lindsley
Craig W
CW
D000478:Alkylation; D001388:Aziridines / Q000737:chemistry*; D002384:Catalysis; D009584:Nitrogen / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
D001388:Aziridines; C033132:aziridine; D009584:Nitrogen