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

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... Full description

Journal Title: Journal of the American Chemical Society 11 March 2015, Vol.137(9), pp.3205-8
Main Author: Yang, Xiaoyu
Other Authors: Toste, F Dean
Format: Electronic Article Electronic Article
Language: English
Subjects:
ID: E-ISSN: 1520-5126 ; PMID: 25719604 Version:1 ; DOI: 10.1021/jacs.5b00229
Link: http://pubmed.gov/25719604
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recordid: medline25719604
title: Direct asymmetric amination of α-branched cyclic ketones catalyzed by a chiral phosphoric acid
format: Article
creator:
  • Yang, Xiaoyu
  • Toste, F Dean
subjects:
  • Ketamine -- Chemical Synthesis
  • Ketones -- Chemistry
  • Phosphoric Acids -- Chemistry
ispartof: Journal of the American Chemical Society, 11 March 2015, Vol.137(9), pp.3205-8
description: 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.
language: eng
source:
identifier: E-ISSN: 1520-5126 ; PMID: 25719604 Version:1 ; DOI: 10.1021/jacs.5b00229
fulltext: fulltext
issn:
  • 15205126
  • 1520-5126
url: Link


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descriptionHere 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.
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titleDirect asymmetric amination of α-branched cyclic ketones catalyzed by a chiral phosphoric acid
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abstractHere 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.
doi10.1021/jacs.5b00229
pmid25719604
issn00027863
date2015-03-11