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1. Phosphine-catalysed α-umpolung addition of nucleophiles to δ-acetoxy allenoates: stereoselective synthesis of 2,4-dienoates

Author

Yuwen Zhang, Yading Hou, and Xiaofeng Tong

Subjects
010405 organic chemistry, Organic Chemistry, Oxide, Conjugated system, 010402 general chemistry, 01 natural sciences, Biochemistry, Combinatorial chemistry, 0104 chemical sciences, Umpolung, chemistry.chemical_compound, chemistry, Nucleophile, Stereoselectivity, Physical and Theoretical Chemistry, Phosphine
Abstract

The first example of phosphine-catalyzed α-umpolung addition of nucleophiles to allenoates is described, which features the use of δ-acetoxy allenoate to generate a 3-phosphonium-2,4-dienoate intermediate, thus facilitating the α-umpolung addition of nucleophiles. Both sulfinate and diarylphosphine oxide are competitive nucleophiles, affording highly activated conjugated dienes with good to excellent stereoselectivities.

Published
2018

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