Asymmetric Synthesis of Dihydrofurans via Rh(II)-catalzed Cyclopropanation-Rearrangement of Enol Ethers with Silanyloxyvinyl Diazoacetates

Muller, Paul; Bernardinelli, Gérald Hugues; Allenbach, Yves; Ferri, Maria; Grass, Stéphane

doi:10.1055/s-2005-868501

Scientific article

Letter

English

Asymmetric Synthesis of Dihydrofurans via Rh(II)-catalzed Cyclopropanation-Rearrangement of Enol Ethers with Silanyloxyvinyl Diazoacetates

ContributorsMuller, Paul; Bernardinelli, Gérald Hugues; Allenbach, Yves; Ferri, Maria; Grass, Stéphane

Published inSynlett, no. 9, p. 1397-1400

Publication date2005

Abstract

The cyclopropanation of dihydrofuran and dihydropyran with methyl 1-(silanyloxy)vinyl diazoacetates in the presence of chiral Rh(II)-catalysts affords cyclopropanes with high diastereo- and enantioselectivitiy. The cyclopropanes, in turn, rearrange to dihydrofurans upon desilylation with TBAF.

Keywords

Carbenes
Catalysis
Diazo compounds
Transition metals
Stereoselectivity

Affiliation entities

Faculté des sciences / Section de chimie et biochimie / Département de chimie organique

Citation (ISO format)

MULLER, Paul et al. Asymmetric Synthesis of Dihydrofurans via Rh(II)-catalzed Cyclopropanation-Rearrangement of Enol Ethers with Silanyloxyvinyl Diazoacetates. In: Synlett, 2005, n° 9, p. 1397–1400. doi: 10.1055/s-2005-868501

Article

Identifiers

PID : unige:7793
DOI : 10.1055/s-2005-868501

Journal ISSN0936-5214

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Asymmetric Synthesis of Dihydrofurans via Rh(II)-catalzed Cyclopropanation-Rearrangement of Enol Ethers with Silanyloxyvinyl Diazoacetates

The cyclopropanation of dihydrofuran and dihydropy­ran with methyl 1-(silanyloxy)vinyl diazoacetates in the presence of chiral Rh(II)-catalysts affords cyclopropanes with high diastereo- and enantioselectivitiy. The cyclopropanes, in turn, rearrange to ­dihydrofurans upon desilylation with TBAF.

Technical informations

The cyclopropanation of dihydrofuran and dihydropyran with methyl 1-(silanyloxy)vinyl diazoacetates in the presence of chiral Rh(II)-catalysts affords cyclopropanes with high diastereo- and enantioselectivitiy. The cyclopropanes, in turn, rearrange to dihydrofurans upon desilylation with TBAF.