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Selective formation of a Z-trisubstituted double bond using a 1-(tert-butyl)tetrazolyl sulfone.

Research paper by Adriana A Lorente, Fernando F Albericio, Mercedes M Álvarez

Indexed on: 04 Oct '14Published on: 04 Oct '14Published in: Journal of Organic Chemistry



Abstract

In our effort to gain further insight into the enantioselective synthesis of the structural core of phormidolides B and C, we have discovered the formation of a Z-trisubstituted double bond. Here, we describe a highly selective process that can be applied to our target following a strategy that is based on Julia-Kocienski olefination. The use of 1-(tert-butyl)tetrazolyl sulfone affords the construction of the Z-trisubstituted alkene with high efficiency and stereoselectivity.