ZnBr2-catalyzed insertions of carbonyl compounds into silacyclopropanes: Regiochemical reversal dependent on metal salt

Annaliese K. Franz; K. A. Woerpel

doi:10.1002/1521-3773(20001201)39:23<4295::AID-ANIE4295>3.0.CO;2-A

ZnBr₂-catalyzed insertions of carbonyl compounds into silacyclopropanes: Regiochemical reversal dependent on metal salt

Annaliese K. Franz, K. A. Woerpel

Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

Surprising catalyst-based regiocontrol: Copper or zinc salts can be employed for the insertion of various carbonyl compounds into silacyclopropanes to afford, respectively, the 1,2- and 1,3-regioisomers of the product with > 99:1 regioselectivity (see scheme). Catalysis by ZnBr₂ allows access to previously unobserved products. The effects of additives such as H₂O, menthol, and di-tert-butylpyridine on the regioselectivity of this insertion process are described.

Original language	English (US)
Pages (from-to)	4295-4299
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	39
Issue number	23
DOIs	https://doi.org/10.1002/1521-3773(20001201)39:23<4295::AID-ANIE4295>3.0.CO;2-A
State	Published - Dec 4 2000

Keywords

Catalysts
Insertions
Silanes
Synthetic methods
Zinc

ASJC Scopus subject areas

Catalysis
General Chemistry

Access to Document

10.1002/1521-3773(20001201)39:23<4295::AID-ANIE4295>3.0.CO;2-A

Cite this

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AB - Surprising catalyst-based regiocontrol: Copper or zinc salts can be employed for the insertion of various carbonyl compounds into silacyclopropanes to afford, respectively, the 1,2- and 1,3-regioisomers of the product with > 99:1 regioselectivity (see scheme). Catalysis by ZnBr2 allows access to previously unobserved products. The effects of additives such as H2O, menthol, and di-tert-butylpyridine on the regioselectivity of this insertion process are described.

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KW - Zinc

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