Formation and utility of azasilacyclopentadienes derived from silacyclopropenes and nitriles

Laura L. Anderson; K. A. Woerpel

doi:10.1021/ol802412b

Formation and utility of azasilacyclopentadienes derived from silacyclopropenes and nitriles

Laura L. Anderson, K. A. Woerpel

Chemistry

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

Abstract

(Chemical Equation Presented) The copper-catalyzed insertions of nitriles into the Si-C bonds of silacyclopropenes provide azasilacyclopentadienes, which can be converted to allylic amines after reduction and protodesilylation. The enamine functionality of azasilacyclopentadienes also participates in 1,4-addition reactions and undergoes a hydroboration and oxidation sequence to form an allylic 1,2-amino alcohol.

Original language	English (US)
Pages (from-to)	425-428
Number of pages	4
Journal	Organic Letters
Volume	11
Issue number	2
DOIs	https://doi.org/10.1021/ol802412b
State	Published - Jan 15 2009

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol802412b

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abstract = "(Chemical Equation Presented) The copper-catalyzed insertions of nitriles into the Si-C bonds of silacyclopropenes provide azasilacyclopentadienes, which can be converted to allylic amines after reduction and protodesilylation. The enamine functionality of azasilacyclopentadienes also participates in 1,4-addition reactions and undergoes a hydroboration and oxidation sequence to form an allylic 1,2-amino alcohol.",

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N2 - (Chemical Equation Presented) The copper-catalyzed insertions of nitriles into the Si-C bonds of silacyclopropenes provide azasilacyclopentadienes, which can be converted to allylic amines after reduction and protodesilylation. The enamine functionality of azasilacyclopentadienes also participates in 1,4-addition reactions and undergoes a hydroboration and oxidation sequence to form an allylic 1,2-amino alcohol.

AB - (Chemical Equation Presented) The copper-catalyzed insertions of nitriles into the Si-C bonds of silacyclopropenes provide azasilacyclopentadienes, which can be converted to allylic amines after reduction and protodesilylation. The enamine functionality of azasilacyclopentadienes also participates in 1,4-addition reactions and undergoes a hydroboration and oxidation sequence to form an allylic 1,2-amino alcohol.

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Formation and utility of azasilacyclopentadienes derived from silacyclopropenes and nitriles

Abstract

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