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Approaches to alpha-amino acids via rearrangement to electron-deficient nitrogen: Beckmann and Hofmann rearrangements of appropriate carboxyl-protected substrates

Chandrasekhar, Sosale and Rao, Mohana V (2012) Approaches to alpha-amino acids via rearrangement to electron-deficient nitrogen: Beckmann and Hofmann rearrangements of appropriate carboxyl-protected substrates. In: Beilstein Journal of Organic Chemistry, 8 . pp. 1393-1399.

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Official URL: http://dx.doi.org/10.3762/bjoc.8.161

Abstract

The titled approaches were effected with various 2-substituted benzoylacetic acid oximes 3 (Beckmann) and 2-substituted malonamic acids 9 (Hofmann), their carboxyl groups being masked as a 2,4,10-trioxaadamantane unit (an orthoacetate). The oxime mesylates have been rearranged with basic Al2O3 in refluxing CHCl3, and the malonamic acids with phenyliodoso acetate and KOH/MeOH. Both routes are characterized by excellent overall yields. Structure confirmation of final products was conducted with X-ray diffraction in selected cases. The final N-benzoyl and N-(methoxycarbonyl) products are alpha-amino acids with both carboxyl and amino protection; hence, they are of great interest in peptide synthesis.

Item Type: Journal Article
Additional Information: Copyright for this article is not available from this repository.
Keywords: amino acid;Beckmann rearrangement;Hofmann rearrangement; orthoacetate;trioxaadamantane
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 23 Nov 2012 06:18
Last Modified: 23 Nov 2012 06:18
URI: http://eprints.iisc.ernet.in/id/eprint/45141

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