American Chemical Society
ja106493h_si_004.pdf (9.44 MB)

Gold-Catalyzed Stereoselective Synthesis of 9-Oxabicyclo[3.3.1]nona-4,7-dienes from Diverse 1-Oxo-4-oxy-5-ynes: A Viable Formal [4 + 2] Cycloaddition on an s-trans-Heterodiene Framework

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journal contribution
posted on 2010-09-15, 00:00 authored by Tse-Min Teng, Arindam Das, Deepak B. Huple, Rai-Shung Liu
We report a highly stereoselective Au-catalyzed synthesis of 9-oxabicyclo[3.3.1]nona-4,7-dienes from diverse 1-oxo-4-oxy-5-ynes. Formation of these highly strained anti-Bredt oxacycles implies the workability of an unprecedented 1,4-dipole of s-trans-methylene(vinyl)oxonium. This work reveals the feasibility of a formal [4 + 2] cycloaddition on an s-trans-heterodiene framework.