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Asymmetric Transfer Hydrogenation Coupled with Dynamic Kinetic Resolution in Water: Synthesis of anti-β-Hydroxy-α-amino Acid Derivatives.

Seashore-Ludlow, Brinton; Saint-Dizier, François and Somfai, Peter LU (2012) In Organic Letters 14(24). p.6334-6337
Abstract
The use of asymmetric transfer hydrogenation combined with dynamic kinetic resolution for the synthesis of β-hydroxy-α-(tert-butoxycarbonyl)amino esters in water is described. This procedure provides the desired amino alcohols in good yields, diastereoselectivities, and enantioselectivities. A surfactant is employed to achieve good yields due to the hydrophobic nature of both the catalyst and substrate. The reaction setup is operationally simple, and nondegassed water can be used as the solvent.
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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Organic Letters
volume
14
issue
24
pages
6334 - 6337
publisher
The American Chemical Society
external identifiers
  • wos:000312564500055
  • pmid:23227944
  • scopus:84871570629
ISSN
1523-7052
DOI
10.1021/ol303115v
language
English
LU publication?
yes
id
cb1d615d-50d3-4c4c-80d6-744b8a8b5ab4 (old id 3347382)
date added to LUP
2013-01-07 10:46:48
date last changed
2017-08-27 03:31:08
@article{cb1d615d-50d3-4c4c-80d6-744b8a8b5ab4,
  abstract     = {The use of asymmetric transfer hydrogenation combined with dynamic kinetic resolution for the synthesis of β-hydroxy-α-(tert-butoxycarbonyl)amino esters in water is described. This procedure provides the desired amino alcohols in good yields, diastereoselectivities, and enantioselectivities. A surfactant is employed to achieve good yields due to the hydrophobic nature of both the catalyst and substrate. The reaction setup is operationally simple, and nondegassed water can be used as the solvent.},
  author       = {Seashore-Ludlow, Brinton and Saint-Dizier, François and Somfai, Peter},
  issn         = {1523-7052},
  language     = {eng},
  number       = {24},
  pages        = {6334--6337},
  publisher    = {The American Chemical Society},
  series       = {Organic Letters},
  title        = {Asymmetric Transfer Hydrogenation Coupled with Dynamic Kinetic Resolution in Water: Synthesis of anti-β-Hydroxy-α-amino Acid Derivatives.},
  url          = {http://dx.doi.org/10.1021/ol303115v},
  volume       = {14},
  year         = {2012},
}