Ambient temperature zincation of N-Boc pyrrolidine and its solvent dependency

Garden, Jennifer A. and Kennedy, Alan R. and Mulvey, Robert E. and Robertson, Stuart D. (2012) Ambient temperature zincation of N-Boc pyrrolidine and its solvent dependency. Chemical Communications, 48 (43). pp. 5265-5267. ISSN 1359-7345 (https://doi.org/10.1039/c2cc31793a)

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Abstract

Sodium TMP-zincate, [(TMEDA)Na(TMP)(Bu-t)Zn(Bu-t)], can deproto-zincate N-Boc pyrrolidine at ambient temperature in hexane solution, whereas in toluene the captured alpha-carbanion of the heterocycle attacks the solvent setting off a cascade of reactions that ultimately produce a pyrrolidine-substituted enolate.

ORCID iDs

Garden, Jennifer A., Kennedy, Alan R. ORCID logoORCID: https://orcid.org/0000-0003-3652-6015, Mulvey, Robert E. ORCID logoORCID: https://orcid.org/0000-0002-1015-2564 and Robertson, Stuart D. ORCID logoORCID: https://orcid.org/0000-0002-9330-8770;
CORE (COnnecting REpositories)