Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 3, Issue 19, Pages 3482-3487Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/b508367b
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The Ti-mediated-reaction of Grignard reagents with nitriles was investigated with sub-stoichiometric amounts of titanium isopropoxide. Cyanoesters were converted to spirocyclopropanelactams in good yields using as low as 0.05 eq of Ti((OPr)-Pr-i)(4). Under similar conditions, cyanocarbonates led to spirocyclopropane oxazolidinones and/or aminocyclopropylcarbinols. A very short synthesis of the naturally occurring aminocyclopropanecarboxylic acid illustrates the usefulness of this methodology.
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