Optically active silicon substituted cyclopropylmethyl alcohols were synthesized through asymmetric Simmons-Smith reaction; that is, the reaction of γ-silicon substituted allylic alcohols with diethylzinc and diiodomethane utilizing (+)-diethyl tartrate as a chiral auxiliary was found to afford the corresponding silicon substituted cyclopropylmethyl alcohols with high stereoselectivity up to 92% ee.
The asymmetric 1,3-dipolar cycloaddition of nitrones possessing electron withdrawing group to an achiral allyl alcohol was achieved by the use of diisopropyl (R,R)-tartrate as a chiral auxiliary to afford the corresponding isoxazolidines with high regio-, diastereo- and enantioselectivity.
The asymmetric 1,3-dipolar cycloaddition of nitrones possessing an electron-withdrawing group to allylic alcohols was achieved by the use of diisopropyl (R,R)-tartrate as a chiral auxiliary to afford the corresponding isoxazolidines with high regio-, diastereo-, and enantioselectivity. In the case of nitrones possessing an electron-withdrawing cyano or t-butoxycarbonyl group, 1,3-dipolar cycloaddition to 2-propen-1-ol occurred to produce the corresponding 3,5-trans-isoxazolidines with high enantioselectivity. To the contrary, nitrones possessing an amide moiety afforded the corresponding optically active 3,5-cis-isoxazolidines with completely opposite diastereoselectivity. A catalytic asymmetric 1,3-dipolar cycloaddition of nitrones possessing the N,N-diisopropylamide moiety to allylic alcohols was achieved to afford di- or trisubstituted isoxazolidines with excellent enantioselectivity of up to over 99% ee. The present asymmetric 1,3-dipolar cycloaddition was applied to the synthesis for the (2S,4R)-4-hydroxyornithine derivative.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.