Add time:07/12/2019 Source:sciencedirect.com
Chiral [(1R)-10-(N,N-diethylsulfamoyl)isobornyl] 2H-azirine 1 [Timén, A. S.; Somfai, P. J. Org. Chem. 2003, 9958–9963; Timén, A. S.; Fisher, A.; Somfai, P. Chem. Commun. 2003, 1150–1151]. was combined to a number of 1,4-disubstituted-2-aza-1,3-dienes 2a–g [Alves, M. J.; Durães, M. M.; Gil Fortes, A. Tetrahedron 2004, 6541–6553] to give cycloadducts 8a–g as major isomers. High to good diastereofacial differentiation of the two faces of the azirine is observed when R1,R2 = Ar 2a–e; diastereoselectivity drops drastically when R1 = Me or H 2f,g. Cycloaddition of the azirine 1 to E,E-1,4-diacetoxy-1,3-butadiene shows complete diastereoselectivity giving cycloadduct 11a.
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