Quantitative α-Alkylation of Primary Nitriles
A synthetic pathway that produces alkyl α,ω-cyanodiolefins in quantitative yield is described, applying chemistry that is based on simple α-alkylation of alkyl nitriles. Three amide bases, lithium 2,2,6,6-tetramethylpiperidide, lithium diisopropylamide, and sodium amide, are used to create the α-car...
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Published in | Synthetic communications Vol. 37; no. 22; pp. 3923 - 3931 |
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Main Authors | , , |
Format | Journal Article |
Language | English |
Published |
PHILADELPHIA
Taylor & Francis Group
01.11.2007
Taylor & Francis |
Subjects | |
Online Access | Get full text |
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Summary: | A synthetic pathway that produces alkyl α,ω-cyanodiolefins in quantitative yield is described, applying chemistry that is based on simple α-alkylation of alkyl nitriles. Three amide bases, lithium 2,2,6,6-tetramethylpiperidide, lithium diisopropylamide, and sodium amide, are used to create the α-carbanions that undergo substitution with various alkylating agents. Optimization leads to essentially quantitative conversions for every substrate/example reported herein, which will prove useful in many synthetic schemes. |
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ISSN: | 0039-7911 1532-2432 |
DOI: | 10.1080/00397910701572456 |