ZnBr2-catalyzed insertions of carbonyl compounds into silacyclopropanes

Regiochemical reversal dependent on metal salt

Annaliese K. Franz, Keith Woerpel

Research output: Contribution to journalArticle

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 languageEnglish (US)
Pages (from-to)4295-4299
Number of pages5
JournalAngewandte Chemie - International Edition
Volume39
Issue number23
DOIs
StatePublished - Dec 4 2000

Fingerprint

Carbonyl compounds
Regioselectivity
Salts
Metals
Menthol
Catalysis
Zinc
Copper
Catalysts

Keywords

  • Catalysts
  • Insertions
  • Silanes
  • Synthetic methods
  • Zinc

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

ZnBr2-catalyzed insertions of carbonyl compounds into silacyclopropanes : Regiochemical reversal dependent on metal salt. / Franz, Annaliese K.; Woerpel, Keith.

In: Angewandte Chemie - International Edition, Vol. 39, No. 23, 04.12.2000, p. 4295-4299.

Research output: Contribution to journalArticle

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