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 language | English (US) |
---|---|
Pages (from-to) | 1601-1614 |
Number of pages | 14 |
Journal | Journal of Organic Chemistry |
Volume | 65 |
Issue number | 6 |
DOIs | |
State | Published - Mar 24 2000 |
ASJC Scopus subject areas
- Organic Chemistry