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Facile and Efficient Enantioselective Hydroxyamination Reaction: Synthesis of 3‐Hydroxyamino‐2‐Oxindoles Using Nitrosoarenes

Angewandte Chemie International EditionPublished 14 April 2011
Ke Shen, Xiaohua Liu, Gang Wang, Lili Lin, Xiaoming Feng
Citations155
SJR quartileQ1
SJR score5.55
SNIP2.47

Abstract

Sc takes action: The highly enantioselective hydroxyamination reaction of N-unprotected 2-oxindoles with nitrosoarenes has been realized using the Sc(OTf)3/L1 complex. The catalyst system exhibited remarkably broad substrate scope and high efficiency. This transformation is the first example of a chiral ScIII/enolate activating a nitrosoarene, and can be conducted on a gram scale without loss in the ee values. Detailed facts of importance to specialist readers are published as "Supporting Information". Such documents are peer-reviewed, but not copy-edited or typeset. They are made available as submitted by the authors. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.

Keywords

Chemistry