Brønsted Acid-Catalyzed Dihydroxylation of Olefins in Aqueous Medium

The trans‐dihydroxylation of olefins occurs efficiently by aqueous hydrogen peroxide catalyzed by p‐toluenesulfonic acid at 50 °C, allowing the catalyst reuse and an outstanding substrate functional group tolerance such as tert‐butoxycarbonylamino (BocNH), benzyloxycarbonylamino (CbzNH), benzyloxy (...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2011-11, Vol.353 (16), p.2920-2926
Main Authors: Rosatella, Andreia A., Afonso, Carlos A. M.
Format: Article
Language:English
Subjects:
1,2‐diols
2-diols
Aliphatic compounds
Amino acids
Catalysis
Catalysts: preparations and properties
Chemistry
dihydroxylation
Exact sciences and technology
Functional groups
General and physical chemistry
Hydrogen peroxide
Olefins
Organic chemistry
Preparations and properties
Reuse
Synthesis
Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
Tolerances
water
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Description
Summary:The trans‐dihydroxylation of olefins occurs efficiently by aqueous hydrogen peroxide catalyzed by p‐toluenesulfonic acid at 50 °C, allowing the catalyst reuse and an outstanding substrate functional group tolerance such as tert‐butoxycarbonylamino (BocNH), benzyloxycarbonylamino (CbzNH), benzyloxy (OBn), tosyloxy (OTs), hindered ketal, (2‐trimethylsilyl)ethoxymethoxy (OSEM), benzylamino (NBz), benzyloxy (OBz) and free amino acid.
ISSN:1615-4150
1615-4169
1615-4169
DOI:10.1002/adsc.201100187