Synthesis 2018; 50(20): 4140-4144
DOI: 10.1055/s-0037-1609562
paper
© Georg Thieme Verlag Stuttgart · New York

Application of the Z-Selective Still–Gennari Olefination Protocol for the Synthesis of Z-α,β-Unsaturated Phosphonates

Centre of Molecular and Macromolecular Studies PAS, Sienkiewicza 112, 90-363 Łódź, Poland   Email: ijanicki@cbmm.lodz.pl
,
Piotr Kiełbasiński
Centre of Molecular and Macromolecular Studies PAS, Sienkiewicza 112, 90-363 Łódź, Poland   Email: ijanicki@cbmm.lodz.pl
› Author Affiliations
The authors would like to thank the National Science Center, Poland, for financial support from grant PRELUDIUM UMO-2016/21/N/ ST5/03361 to I. J.
Further Information

Publication History

Received: 18 May 2018

Accepted after revision: 20 June 2018

Publication Date:
23 July 2018 (online)


Abstract

Application of the Z-selective Still–Gennari modification of Horner–Wadsworth–Emmons (HWE) reaction for the olefination of acylphosphonates is presented. A series of new Z-α,β-unsaturated phosphonates containing a carbonyl or ester moiety in the β-position were obtained in up to 94% yield and with up to 96% Z-selectivity. The standard HWE olefination of the acylphosphonates, which was performed for comparison, was either unsuccessful at all, or resulted in an inferior Z-selectivity and lower isolated yields.

Supporting Information

 
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