Journal
CHEMICAL SCIENCE
Volume 3, Issue 10, Pages 2949-2957Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c2sc20590d
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Funding
- University of the Basque Country UPV/EHU [UFI QOSYC 11/22]
- Basque Government (GV) [IT-291-07]
- Ministerio de Educacion y Ciencia (MEC), Spain [CTQ2007-68095-C02-01]
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The first enamine mediated anti-selective and highly enantioselective Mannich reaction of aldehydes and unactivated imines is reported. The key for success is the combined use of a Bronsted acid with an alpha,alpha-dialkylprolinol ether catalyst that leads to adducts with good yields (typically 70-75%), anti : syn ratios greater than 90 : 10, and ee values usually above 95%. The method works particularly well with propargylic imines and, unlike previous catalytic routes to optically active propargylamines, provides adducts featuring two contiguous stereocenters and a functionalized side chain amenable for ulterior synthetic applications.
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