A Stereoselective Access to Functional Dienes Containing a Trifluoromethyl Group <i>via</i> Stille Cross Coupling of Ethyl 4,4,4-Trifluoro-3-iodobutenoate

Gildas Prié, Jérôme Thibonnet, Mohamed Abarbri, Alain Duchêne, Jean‐Luc Parrain

Synlett · 1998 · 32 citations · 0 references

Concepts

Abstract

(opens in new window) Buy Article (opens in new window) Permissions and Reprints (opens in new window) All articles of this category (opens in new window) Stereoselective construction of 3-trifluoromethyl conjugated dienoates or enynoates was achieved from ethyl ( Z )-4,4,4-trifluoro-3-iodobutenoate and alkenyltin or alkynyltin reagents through the Stille reaction. Reduction of ethyl 3-trifluoromethyldienoates using DIBAL-H selectively afforded allylic alcohols. conjugated 3-trifluoromethyl dienoates or dienols - Stille cross-coupling reaction - vinyltin reagents - vinylic iodide - substitution - reduction