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

被引：5

作者：

Shimada, Y

Akane, H

Taniguchi, N

Matsuhisa, A

Kawano, N

Tanaka, A

机构：

[1] Yamanouchi Pharmaceut Co Ltd, Inst Drug Discovery Res, Tsukuba, Ibaraki 3058585, Japan

[2] Yamanouchi Pharmaceut Co Ltd, Clin Dev Dept, Tokyo 1748612, Japan

[3] Yamanouchi Pharmaceut Co Ltd, Dept Commun, Chuo Ku, Tokyo 1038411, Japan

来源：

CHEMICAL & PHARMACEUTICAL BULLETIN | 2005年 / 53卷 / 05期

关键词：

arginine vasopressin antagonist; dianion; Horner-Wadsworth-Emmons reaction;

D O I：

10.1248/cpb.53.589

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Stereoselective synthesis of m ethyl (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.

引用

页码：589 / 590

页数：2

共 7 条

[1]

Ager D. J., 1990, ORG REACTIONS, V38, P1, DOI DOI 10.1002/0471264180.0R038.01

[2]

DIXON DA, 1991, SELECTIVE FLUORINATI, pCH2

[3]

KOPPEL GA, 1974, TETRAHEDRON LETT, V15, P711

[4] THE WITTIG OLEFINATION REACTION AND MODIFICATIONS INVOLVING PHOSPHORYL-STABILIZED CARBANIONS - STEREOCHEMISTRY, MECHANISM, AND SELECTED SYNTHETIC ASPECTS [J].