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Bis(2,2,2-trifluoroethyl)bromophosphonoacetate, a Novel HWE Reagent for the Preparation of (E)-α-Bromoacrylates:  A General and Stereoselective Method for the Synthesis of Trisubstituted Alkenes

Keiko Tago and Hiroshi Kogen*

*Exploratory Chemistry Research Laboratories, Sankyo Co., Ltd., 2-58, Hiromachi, 1-chome Shinagawa-ku, Tokyo, 140-8710 Japan, Email:

K. Tago, H. Kogen, Org. Lett., 2000, 2, 1975-1978.

DOI: 10.1021/ol006074x


Horner-Wadsworth-Emmons (HWE) reactions of bis(2,2,2-trifluoroethoxy)bromophosphonoacetate with various aldehydes in the presence of t-BuOK and 18-C-6 provide (E)-α-bromoacrylates with high stereoselectivity, which are useful precursors for various C-C bond formations.

see article for more examples


Improved Preparation of Methyl Bis(2,2,2-trifluoroethoxy)bromophosphonoacetate for the Stereoselective Synthesis of (E)-α-Bromoacrylates:
A. Nakata, K. Kobayashi, H. Kogen, Chem. Pharm. Bull. 2013, 61, 108-110.

Hiroshi Kogen, September 23, 2020

Key Words

Wittig-Horner Reaction, alkenyl bromides, unsaturated esters

ID: J54-Y2000