Stereoselective Synthesis of (Z)- and (E)-Allylic Silanes by Copper-Mediated Substitution Reactions of Allylic Carbamates with Grignard Reagents

Jacqueline H. Smitrovich, K. A. Woerpel

Research output: Contribution to journalArticle

Abstract

Both (Z)- and (E)-allylic silanes were prepared with high stereoselectivity by the copper-mediated substitution of allylic carbamates by organometallic reagents. The reaction of alkylmagnesium reagents with (E)-allylic carbamates provides (Z)-allylic silanes, whereas both alkylmagnesium and alkyllithium reagents react with (Z)-allylic carbamates to afford (E)-allylic silanes. Because Grignard reagents are often more facile to prepare than alkyllithium species, these reagents are the optimal nucleophiles for the synthesis of both (Z)- and (E)-allylic silanes. This method also allows readily available nonracemic allylic carbamates to be converted to chiral, nonracemic (Z)-and (E)-allylic silanes with high stereoselectivity.

Original languageEnglish (US)
Pages (from-to)1601-1614
Number of pages14
JournalJournal of Organic Chemistry
Volume65
Issue number6
DOIs
StatePublished - Mar 24 2000

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Silanes
Carbamates
Copper
Substitution reactions
Stereoselectivity
Nucleophiles
Organometallics

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Stereoselective Synthesis of (Z)- and (E)-Allylic Silanes by Copper-Mediated Substitution Reactions of Allylic Carbamates with Grignard Reagents. / Smitrovich, Jacqueline H.; Woerpel, K. A.

In: Journal of Organic Chemistry, Vol. 65, No. 6, 24.03.2000, p. 1601-1614.

Research output: Contribution to journalArticle

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