Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 67, Issue 11, Pages 3965-3968Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo025634y
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alpha-Alkoxy, amino-, and thio nitriles under-go a Ti(II)-mediated coupling with Grignard reagents to afford heterofunctionalized cyclopropylamines. A chelation effect appears to be generally responsible for the spontaneous contraction of the intermediate azatitanacycle leading to cyclopropane. By using the described reaction, 1-amino-cyclopropanecarboxylic acids were prepared in four steps, in good overall yields, from the readily available benzyloxy-acetonitrile.
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