Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 137, Issue 9, Pages 3205-3208Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.5b00229
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Funding
- NIHGMS [R01 GM104534]
- SIOC
- Zhejiang Medicine
- Pharmaron
- NIH [S10-RR027172]
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Here we report the direct asymmetric amination of alpha-substituted cyclic ketones catalyzed by a chiral phosphoric acid, yielding products with a N-containing quaternary stereocenter in high yields and excellent, enantioselectivities. Kinetic resolution of the starting ketone was also found to occur on some of the substrates under milder conditions, providing enantioenriched alpha-branched ketones, another important building block in organic synthesis. The utility of this methodology was demonstrated in the short synthesis of (S)-ketamine, the more active enantiomer of this versatile pharmaceutical.
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