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Supramolecular Catalysis of Strecker Reaction in Water under Neutral Conditions in the Presence of β-Cyclodextrin^†

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K. Surendra, N. Srilakshmi Krishnaveni, A. Mahesh, and K. Rama Rao*

Organic Chemistry Division-I, Indian Institute of Chemical Technology, Hyderabad-500 007, India drkrrao@yahoo.com

J. Org. Chem., 2006, 71 (6), pp 2532–2534

DOI: 10.1021/jo052510n

Publication Date (Web): February 23, 2006

†

IICT communication no. 060116.

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

Abstract

An environmentally benign and highly efficient procedure for the nucleophilic addition of trimethylsilyl cyanide to imines (Strecker reaction) has been developed under biomimetic conditions in water in the presence of β-cyclodextrin to afford α-aminonitriles in quantitative yields. The use of cyclodextrin precludes the use of either acid or base, and the catalyst can be recycled a number of times without loss in activity.

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Published In Issue March 17, 2006
Received December 6, 2005

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Note

Supramolecular Catalysis of Strecker Reaction in Water under Neutral Conditions in the Presence of β-Cyclodextrin^†