Journal
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA
Volume 115, Issue 8, Pages 1730-1735Publisher
NATL ACAD SCIENCES
DOI: 10.1073/pnas.1718474115
Keywords
phase-transfer catalysis; umpolung; asymmetric tandem reactions; chemoselectivity; chiral amines
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Funding
- National Institutes of Health [GM-61591]
- Keck Foundation
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This paper describes the mechanistic insight-guided development of a catalyst system, employing a phenolic proton donor catalyst in addition to a cinchonium-derived phase-transfer catalyst, to control the chemoselectivity of two distinct intermediates, thereby enabling the desired asymmetric tandem conjugate addition-protonation pathway to dominate over a number of side-reaction pathways to provide a synthetic approach for the direct generation of optically active amines bearing two nonadjacent stereocenters.
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