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Highly enantioselective aryl transfer to aldehydes: a remarkable effect of sulfur substitution in amino thioacetate ligands.

Authors
  • Jin, Myung-Jong1
  • Sarkar, Shaheen M
  • Lee, Dong-Hwan
  • Qiu, Huili
  • 1 School of Chemical Science and Engineering, Inha University, Incheon 402-751, South Korea. [email protected] , (North Korea)
Type
Published Article
Journal
Organic Letters
Publisher
American Chemical Society
Publication Date
Mar 20, 2008
Volume
10
Issue
6
Pages
1235–1237
Identifiers
DOI: 10.1021/ol8001249
PMID: 18288855
Source
Medline
License
Unknown

Abstract

Chiral amino thioacetate ligands were prepared from the corresponding amino alcohols and used as catalysts for enantioselective aryl transfer reaction. The amino thioacetates were remarkably superior to the corresponding amino alcohols. Low catalyst loadings of only 1-2.5 mol % were sufficient to achieve excellent enantioselectivity as well as high conversion in short reaction time. The results reveal that the thioacetoxy moiety of the amino thioacetates has a surprisingly beneficial effect in enhancing the asymmetric induction.

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