Przejdź do zawartości
Merck

Asymmetric synthesis of cyclopropylamines starting from N-sulfinyl alpha-chloro ketimines.

Organic letters (2007-01-16)
Bram Denolf, Sven Mangelinckx, Karl W Törnroos, Norbert De Kimpe
ABSTRAKT

Treatment of novel chiral N-sulfinyl alpha-chloro ketimines with Grignard reagents resulted in the synthesis of chiral N-(1-substituted cyclopropyl)-tert-butanesulfinamides in acceptable to good yields and diastereoselectivity via 1,3-dehydrohalogenation and subsequent addition of the Grignard reagent to the intermediate cyclopropylideneamine. Only in the case of allylmagnesium chloride did the reaction lead to aziridines in high yield. Further deprotection toward N-unprotected 1-substituted cyclopropylamines was established, and the absolute configuration was determined. [reaction: see text].

MATERIAŁY
Numer produktu
Marka
Opis produktu

Sigma-Aldrich
Cyclopropylamine, 98%