A Novel Stereocontrolled Synthesis of Cyclopropyl-Substituted α,β-Unsaturated Esters: Palladium Catalyzed Cross-coupling of Cyclopropylboronic Acids with Bromoacrylates

Shao-Man Zhou; Yi-Long Yan; Min-Zhi Deng

doi:10.1055/s-1998-863093

Synlett 1998; 1998(2): 198-200
DOI: 10.1055/s-1998-863093

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A Novel Stereocontrolled Synthesis of Cyclopropyl-Substituted α,β-Unsaturated Esters: Palladium Catalyzed Cross-coupling of Cyclopropylboronic Acids with Bromoacrylates

Shao-Man Zhou^* , Yi-Long Yan, Min-Zhi Deng

^*Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China; Fax 00 86-21-64 16 61 28

Abstract

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A novel method of stereocontrolled preparing some cyclopropyl substituted α,β-unsaturated esters is described, based upon the palladium catalyzed cross-coupling reaction of bromoacrylates with trans-2-alkyl(aryl)cyclopropylboronic acids. It was found that using toluene as a solvent and in the presence of K₃PO₄ · 3 H₂O and catalytic amount of Pd(PPh₃)₄ the bromoacrylates could readily take part in the cross-coupling reaction with cyclopropylboronic acids at 100 °C, giving corresponding stereodefined cyclopropyl substituted α,β-unsaturated esters in good to excellent yields.

cyclopropylboronic acid - bromoacrylate - Suzuki reaction - palladium catalyzed cross-coupling - cyclopropyl-substituted α,β-unsaturated ester

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