Stereoselective Synthesis of Methyl (Z)-(4,4-Difluoro-2,3,4,5-tetrahydro-1H-1-benzazepin-5-ylidene)acetate Using a Dianion Horner–Wadsworth–Emmons Reagent

Yoshiaki Shimada; Hiroaki Akane; Nobuaki Taniguchi; Akira Matsuhisa; Noriyuki Kawano; Akihiro Tanaka

doi:10.1248/cpb.53.589

Notes

Stereoselective Synthesis of Methyl (Z)-(4,4-Difluoro-2,3,4,5-tetrahydro-1H-1-benzazepin-5-ylidene)acetate Using a Dianion Horner–Wadsworth–Emmons Reagent

Yoshiaki Shimada, Hiroaki Akane, Nobuaki Taniguchi, Akira Matsuhisa, Noriyuki Kawano, Akihiro Tanaka

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Keywords: arginine vasopressin antagonist, dianion, Horner–Wadsworth–Emmons reaction

JOURNAL FREE ACCESS

2005 Volume 53 Issue 5 Pages 589-590

DOI https://doi.org/10.1248/cpb.53.589

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Abstract

Stereoselective synthesis of methyl (Z)-(4,4-difluoro-2,3,4,5-tetrahydro-1H-1-benzazepin-5-ylidene)acetate (1a) is described. Z-selectivity of the Horner–Wadsworth–Emmons (HWE) reaction was obtained based on an investigation of the reaction conditions for introduction of a methylidene group onto the 5-position of benzazepine.

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