General, Robust, and Stereocomplementary Preparation of α,β-Disubstituted α,β-Unsaturated Esters
- 28 August 2009
- journal article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 11 (19), 4258-4261
- https://doi.org/10.1021/ol9013359
Abstract
An (E)- and (Z)-stereocomplementary preparative method for α,β-disubstituted α,β-unsaturated esters is performed via three general and robust reaction sequences: (i) Ti−Claisen condensation (formylation) of esters to give α-formyl esters (12 examples, 60−99%), (ii) (E)- and (Z)-stereocomplementary enol p-toluenesulfonylation (tosylation) using TsCl−N-methylimidazole (NMI)−Et3N and LiOH (24 examples, 82−99%), and (iii) stereoretentive Suzuki−Miyaura cross-coupling (18 examples, 64−96%).Keywords
This publication has 25 references indexed in Scilit:
- Stereoselective Synthesis of Acetoacetate-Derived Enol TriflatesOrganic Letters, 2008
- General, Robust, and Stereocomplementary Preparation of β-Ketoester Enol Tosylates as Cross-Coupling Partners Utilizing TsCl−N-Methylimidazole AgentsOrganic Letters, 2008
- Stereoselective Synthesis of Z-α-Aryl-α,β-unsaturated EstersThe Journal of Organic Chemistry, 2006
- Structure–activity relationships of the peptide deformylase inhibitor BB-3497: modification of the methylene spacer and the P1′ side chainBioorganic & Medicinal Chemistry Letters, 2003
- An (E)-selective synthesis of trisubstituted (E)-α,β-unsaturated acid derivativesChemical Communications, 2003
- Rhodium-Catalyzed Hydroarylation of Alkynes with Arylboronic Acids: 1,4-Shift of Rhodium from 2-Aryl-1-alkenylrhodium to 2-Alkenylarylrhodium IntermediateJournal of the American Chemical Society, 2001
- Facile stereoselective syntheses of (E)- and (Z) -α-substituted cinnamates by stereoselective dehydration reaction with 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC)Tetrahedron Letters, 1999
- The Selective Claisen and Dieckmann Ester Condensations Promoted by Dichlorobis(trifluoromethanesulfonato)titanium(IV)Bulletin of the Chemical Society of Japan, 1989
- H2‐Antihistaminika, 18. Mitt. 5,6‐Alkylsubstituierte 4‐Pyrimidinone mit H2‐antihistaminischer WirkungArchiv der Pharmazie, 1984
- Overlap Control of Carbanionoid Reactions. II.1 The Stereochemistry of the Perkin Reaction and Related Condensation ReactionsJournal of the American Chemical Society, 1959