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
- 1 January 2005
- journal article
- Published by Pharmaceutical Society of Japan in CHEMICAL & PHARMACEUTICAL BULLETIN
- Vol. 53 (5) , 589-590
- https://doi.org/10.1248/cpb.53.589
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.Keywords
This publication has 5 references indexed in Scilit:
- Highly Potent and Orally Active Non-Peptide Arginine Vasopressin Antagonists for Both V1A and V2 Receptors: Synthesis and Pharmacological Properties of 4'-[(4,4-Difluoro-5-methylidene-2,3,4,5-tetrahydro-1H-1-benzoazepin-1-yl)carbonyl]-2-phenylbenzanililde Derivatives.CHEMICAL & PHARMACEUTICAL BULLETIN, 2000
- Highly Diastereoselective Michael Addition Reactions of Lithium Enolates to Ethyl 3-TrifluoromethylacrylateChemistry Letters, 1991
- The Wittig olefination reaction and modifications involving phosphoryl-stabilized carbanions. Stereochemistry, mechanism, and selected synthetic aspectsChemical Reviews, 1989
- Carboxyvinylation; a one-step synthesis of α,β-unsaturated acidsTetrahedron Letters, 1974
- The Utility of Phosphonate Carbanions in Olefin SynthesisJournal of the American Chemical Society, 1961