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Copper-Catalyzed Enantio- and Diastereoselective Addition of Silicon Nucleophiles to 3,3-Disubstituted Cyclopropenes.

ABSTRACT: A highly stereocontrolled syn-addition of silicon nucleophiles across cyclopropenes with two different geminal substituents at C3 is reported. Diastereomeric ratios are excellent throughout (d.r.≥98:2) and enantiomeric excesses usually higher than 90 %, even reaching 99 %. This copper-catalyzed C-Si bond formation closes the gap of the direct synthesis of α-chiral cyclopropylsilanes.

SUBMITTER: Zhang L

PROVIDER: S-EPMC6899982 | biostudies-literature | 2019 Nov

REPOSITORIES: biostudies-literature

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Copper-Catalyzed Enantio- and Diastereoselective Addition of Silicon Nucleophiles to 3,3-Disubstituted Cyclopropenes.

Zhang Liangliang L Oestreich Martin M

Chemistry (Weinheim an der Bergstrasse, Germany) 20191022 63

A highly stereocontrolled syn-addition of silicon nucleophiles across cyclopropenes with two different geminal substituents at C3 is reported. Diastereomeric ratios are excellent throughout (d.r.≥98:2) and enantiomeric excesses usually higher than 90 %, even reaching 99 %. This copper-catalyzed C-Si bond formation closes the gap of the direct synthesis of α-chiral cyclopropylsilanes. ...[more]

PMID: 31531992

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