title: Copper-Catalyzed Asymmetric Propargylation of Cyclic Aldimines.
abstract: 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.
authors.affiliation: 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.
authors.forename: Daniel R
authors.initials: DR
authors.lastname: Fandrick
authors.affiliation: Department of Chemistry, Wayne State University , 5101 Cass Avenue, Detroit, Michigan 48202, United States.
authors.forename: Christine A
authors.initials: CA
authors.lastname: Hart
authors.affiliation: 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.
authors.forename: Ifeanyi S
authors.initials: IS
authors.lastname: Okafor
authors.affiliation: 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.
authors.forename: Michael A
authors.initials: MA
authors.lastname: Mercadante
authors.affiliation: 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.
authors.forename: Sanjit
authors.initials: S
authors.lastname: Sanyal
authors.affiliation: 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.
authors.forename: James T
authors.initials: JT
authors.lastname: Masters
authors.affiliation: 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.
authors.forename: Max
authors.initials: M
authors.lastname: Sarvestani
authors.affiliation: 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.
authors.forename: Keith R
authors.initials: KR
authors.lastname: Fandrick
authors.affiliation: Department of Chemistry, Wayne State University , 5101 Cass Avenue, Detroit, Michigan 48202, United States.
authors.forename: Jennifer L
authors.initials: JL
authors.lastname: Stockdill
authors.affiliation: 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.
authors.forename: Nelu
authors.initials: N
authors.lastname: Grinberg
authors.affiliation: 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.
authors.forename: Nina
authors.initials: N
authors.lastname: Gonnella
authors.affiliation: 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.
authors.forename: Heewon
authors.initials: H
authors.lastname: Lee
authors.affiliation: 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.
authors.forename: Chris H
authors.initials: CH
authors.lastname: Senanayake