Solvent-Free Organocatalytic
Mukaiyama-Michael Addition of 2-Trimethylsilyloxy
Furan to Nitroalkenes Catalyzed by Brønsted Acids

Arrigo Scettri; Vincenzo De Sio; Rosaria Villano; Maria Rosaria Acocella

doi:10.1055/s-0029-1217970

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Synlett 2009(16): 2629-2632
DOI: 10.1055/s-0029-1217970

LETTER

Solvent-Free Organocatalytic Mukaiyama-Michael Addition of 2-Trimethylsilyloxy Furan to Nitroalkenes Catalyzed by Brønsted Acids

Arrigo Scettri*^a, Vincenzo De Sio^a, Rosaria Villano^b, Maria Rosaria Acocella*^a
^a Dipartimento di Chimica, Università di Salerno, Via Ponte Don Melillo, 84084 Fisciano (Salerno), Italy
Fax: +39(089)969603; e-Mail: scettri@unisa.it;
^b Istituto di Chimica Biomolecolare del CNR, Traversa La Crucca 3, 07040 Li Punti (Sassari), Italy

Further Information

Publication History

Received 10 July 2009
Publication Date:
09 September 2009 (online)

Abstract
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Abstract

The first organocatalytic Mukaiyama-Michael addition of 2-trimethylsilyloxy furan to nitroalkenes was promoted by Brønsted acids under solvent-free conditions. The conjugate addition took place in moderate to good yields with variously substituted nitroalkenes. The procedure is operationally simple and no workup is required.

Key words

solvent-free - conjugate addition - Brønsted acids - nitroalkenes - 2-trimethylsilyloxy furan

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General Procedure
The reaction was carried out in a dry vial. Nitrostyrene (149 mg, 1.0mmol) and 2-trimethylsilyloxy furan (200 µL, 1.2 mmol) were added to the catalyst (5 mol%) at -20 ˚C. The reaction mixture was stirred at the same temperature for
the time indicated. The crude was purified by column chromatography on silica gel in gradient elution with PE-EtOAc to obtain the pure product.