ChemInform Abstract: Sulfinylimidates as Chiral Amide Equivalents for Irreversible, Asymmetric Aldol Reactions.

Metal Free, Microwave Assisted Preparation of N-Sulfonyl and N-Sulfinyl Imines and Imidates

“…N-Sulfonylimidates Synthesis. With two efficient methods for the synthesis of sulfonyl and sulfinyl imines from acetals, and being also interested in imidates, 6,35 we next considered applying similar conditions to the preparation of Nsulfonyl-and N-sulfinylimidates from orthoesters. N-Sulfonylimidates have mainly been used in diastereoselective αalkylation reactions, 3,4,35 and can easily be converted into amides or esters, whereas N-sulfinylimidates have found applications in diastereoselective alkylations, 36 Mannich-type condensations, 37 conjugate additions, 38 and diastereoselective aldol-type reactions.…”

“…N-Sulfonylimidates have mainly been used in diastereoselective αalkylation reactions, 3,4,35 and can easily be converted into amides or esters, whereas N-sulfinylimidates have found applications in diastereoselective alkylations, 36 Mannich-type condensations, 37 conjugate additions, 38 and diastereoselective aldol-type reactions. 6 A few methods have been described for the preparation of such imidates, which suffer of long reaction time and tedious procedures. The most general approach for the preparation of N-sulfonylimidates consists in the formation of a Pinner salt from a nitrile followed by N-tosylation.…”