M. I. Pleshchev, V. V. Kachala, A. S. Goloveshkin, I. S. Bushmarinov, V. V. Kuznetsov, D. V. Khakimov, N. N. Makhova, “Unexpected regioselectivities of [3 + 2] cycloaddition of azomethine imines to acrylonitrile and 4-nitrophenyl vinyl sulfone”, Mendeleev Commun., 2013, Volume 23, Issue 5,Pages <nobr>271

This article is cited in 25 papers

Communications

Unexpected regioselectivities of [3 + 2] cycloaddition of azomethine imines to acrylonitrile and 4-nitrophenyl vinyl sulfone

M. I. Pleshchev^a, V. V. Kachala^a, A. S. Goloveshkin^b, I. S. Bushmarinov^b, V. V. Kuznetsov^a, D. V. Khakimov^a, N. N. Makhova^a

^a N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation
^b A.N. Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences, Moscow, Russian Federation

Abstract: The [3 + 2] cycloaddition of azomethine imines derived from 6-aryl-1,5-diazabicyclo[3.1.0]hexanes to acrylonitrile and 4-nitrophenyl vinyl sulfone proceeds with high diastereoselectivity, but with opposite regioselectivity, which has been clarified by quantum chemical calculations.

Language: English

DOI: 10.1016/j.mencom.2013.09.011