Copper-Catalyzed Asymmetric Propargylation of Cyclic Aldimines.

Autor:	Fandrick DR; Chemical Development and Material and Analytical Sciences, Boehringer-Ingelheim Pharmaceuticals, Inc., 900 Old Ridgebury Road/P.O. Box 368, Ridgefield, Connecticut 06877-0368, United States., Hart CA; Department of Chemistry, Wayne State University , 5101 Cass Avenue, Detroit, Michigan 48202, United States., Okafor IS; Chemical Development and Material and Analytical Sciences, Boehringer-Ingelheim Pharmaceuticals, Inc., 900 Old Ridgebury Road/P.O. Box 368, Ridgefield, Connecticut 06877-0368, United States., Mercadante MA; Chemical Development and Material and Analytical Sciences, Boehringer-Ingelheim Pharmaceuticals, Inc., 900 Old Ridgebury Road/P.O. Box 368, Ridgefield, Connecticut 06877-0368, United States., Sanyal S; Chemical Development and Material and Analytical Sciences, Boehringer-Ingelheim Pharmaceuticals, Inc., 900 Old Ridgebury Road/P.O. Box 368, Ridgefield, Connecticut 06877-0368, United States., Masters JT; Chemical Development and Material and Analytical Sciences, Boehringer-Ingelheim Pharmaceuticals, Inc., 900 Old Ridgebury Road/P.O. Box 368, Ridgefield, Connecticut 06877-0368, United States., Sarvestani M; Chemical Development and Material and Analytical Sciences, Boehringer-Ingelheim Pharmaceuticals, Inc., 900 Old Ridgebury Road/P.O. Box 368, Ridgefield, Connecticut 06877-0368, United States., Fandrick KR; Chemical Development and Material and Analytical Sciences, Boehringer-Ingelheim Pharmaceuticals, Inc., 900 Old Ridgebury Road/P.O. Box 368, Ridgefield, Connecticut 06877-0368, United States., Stockdill JL; Department of Chemistry, Wayne State University , 5101 Cass Avenue, Detroit, Michigan 48202, United States., Grinberg N; Chemical Development and Material and Analytical Sciences, Boehringer-Ingelheim Pharmaceuticals, Inc., 900 Old Ridgebury Road/P.O. Box 368, Ridgefield, Connecticut 06877-0368, United States., Gonnella N; Chemical Development and Material and Analytical Sciences, Boehringer-Ingelheim Pharmaceuticals, Inc., 900 Old Ridgebury Road/P.O. Box 368, Ridgefield, Connecticut 06877-0368, United States., Lee H; Chemical Development and Material and Analytical Sciences, Boehringer-Ingelheim Pharmaceuticals, Inc., 900 Old Ridgebury Road/P.O. Box 368, Ridgefield, Connecticut 06877-0368, United States., Senanayake CH; Chemical Development and Material and Analytical Sciences, Boehringer-Ingelheim Pharmaceuticals, Inc., 900 Old Ridgebury Road/P.O. Box 368, Ridgefield, Connecticut 06877-0368, United States.
Jazyk:	angličtina
Zdroj:	Organic letters [Org Lett] 2016 Dec 02; Vol. 18 (23), pp. 6192-6195. Date of Electronic Publication: 2016 Nov 22.
DOI:	10.1021/acs.orglett.6b03253
Abstrakt:	The copper-catalyzed asymmetric propargylation of cyclic aldimines is reported. The influence of the imine trimer to inhibit the reaction was identified, and equilibrium constants between the monomer and trimer were determined for general classes of imines. Asymmetric propargylation of a diverse series of N-alkyl and N-aryl aldimines was achieved with good to high asymmetric induction. The utility was demonstrated by a titanium catalyzed hydroamination and reduction to generate the chiral indolizidines (-)-crispine A and (-)-harmicine.
Databáze:	MEDLINE
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