Tuesday, October 22, 2013

Highly Enantioselective Synthesis of Chiral 7-Ring O- and N-Heterocycles by a One-pot Nitro-Michael/Cyclization Tandem Reaction

by Renate Rohlmann, Constantin Gabriel Daniliuc, Olga Garcia Mancheno*

A concise enantioselective approach to medium-sized 7-ring O- and N-heterocycles has been developed. The synthetic strategy relies on an organocatalytic nitro-Michael/nitrile oxide cycloaddition tandem reaction, leading to the corresponding chiral benzoxe- and benzazepine derivatives containing an additional fused dihydroisoxazoline ring in good yields and excellent enantioselectivities (up to 97% ee).

Chemical Communications


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