Chiral Brønsted Acid Catalyzed Pinacol Rearrangement

Asymmetric pinacol rearrangement: The pinacol rearrangement has long been known to be difficult to control in terms of regioselectivity and stereoselectivity. It has been found that indolyl diols can be treated with chiral phosphoric acids to effect a regio‐ and enantioselective pinacol rearrangemen...

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Bibliographic Details
Published in:Angewandte Chemie (International ed.) 2010-12, Vol.49 (50), p.9734-9736
Main Authors: Liang, Tao, Zhang, Zhenjie, Antilla, Jon C
Format: Article
Language:English
Subjects:
asymmetric catalysis
Catalysis
Glycols - chemistry
Indoles - chemistry
indolyl diols
organocatalysis
phosphoric acids
Phosphoric Acids - chemistry
pinacol rearrangement
Stereoisomerism
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Summary:Asymmetric pinacol rearrangement: The pinacol rearrangement has long been known to be difficult to control in terms of regioselectivity and stereoselectivity. It has been found that indolyl diols can be treated with chiral phosphoric acids to effect a regio‐ and enantioselective pinacol rearrangement with high efficiency (see scheme; Ar=1‐naphthyl).
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201004778