ol7b00468_si_002.cif (1.1 MB)
Diastereoselective Base-Catalyzed Formal [4 + 2] Cycloadditions of N‑Sulfonyl Imines and Cyclic Anhydrides
dataset
posted on 2017-05-04, 21:04 authored by Stephen
W. Laws, Lucas C. Moore, Michael J. Di Maso, Q. Nhu N. Nguyen, Dean J. Tantillo, Jared T. ShawA diastereoselective
base-catalyzed Mannich reaction of cyclic,
enolizable anhydrides and N-sulfonyl imines for the
synthesis of δ-lactams is reported. This anhydride Mannich reaction
tolerates imines derived from aryl and enolizable aldehydes. A base-catalyzed
product epimerization pathway ensures high anti diastereoselectivity
in aryl and achiral enolizable imines.