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J Am Chem Soc. 2015 Mar 11;137(9):3205-8. doi: 10.1021/jacs.5b00229. Epub 2015 Feb 26.

Direct asymmetric amination of α-branched cyclic ketones catalyzed by a chiral phosphoric acid.

Author information

1
Department of Chemistry, University of California , Berkeley, California 94720, United States.

Abstract

Here we report the direct asymmetric amination of α-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 α-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.

PMID:
25719604
PMCID:
PMC4562282
DOI:
10.1021/jacs.5b00229
[Indexed for MEDLINE]
Free PMC Article

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