Tetrahedron Letters

Anomalous Z-isomer content in Wittig reaction products from keto-stabilised ylides with ortho-heteroatom substituted benzaldehydes

PA Byrne, LJ Higham, P McGovern, DG Gilheany

Index: Byrne, Peter A.; Higham, Lee J.; McGovern, Padraic; Gilheany, Declan G. Tetrahedron Letters, 2012 , vol. 53, # 49 p. 6701 - 6704

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Citation Number: 7

Abstract

Wittig reaction products of keto-stabilised ylides with ortho-substituted benzaldehydes are found to show significantly higher than expected Z-alkene content (up to 50%) compared to analogous reactions of the same ylides with benzaldehyde itself. A cooperative effect is seen whereby the unusual Z-content is further augmented if the ylide bears greater steric bulk in the α′-position. These results are consistent with our previous observations on ...

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