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An unexpected transformation of benzyl carbamates into alpha-azidobenzeneacetamides


Strässler, Christof; Heimgartner, Heinz (1997). An unexpected transformation of benzyl carbamates into alpha-azidobenzeneacetamides. Helvetica Chimica Acta, 80:2058-2065.

Abstract

Successive treatment of benzyl carbamates 5 (Z-protected secondary amines) with lithium diisopropylamide (LDA), diphenyl phosphorochloridate (DPPCl), and NaN3 yielded the corresponding alpha-azidobenzeneacetamides 6 in 45-50% yield (Schemes 2 and 3). In the case of Z-protected diisopropylamine 5b, the phosphate 7 was isolated as a minor product. A reaction mechanism for this unexpected transformation is proposed in Scheme 4, the key step being the ring closure of a benzylic anion to give an oxirane intermediate B. In cursory experiments, it was demonstrated that alpha-azidobenzeneacetamides 6 can be used as 2-phenylglycine synthons in the formation of dipeptides by using a phosphine-mediated coupling (Scheme 5 ) .

Abstract

Successive treatment of benzyl carbamates 5 (Z-protected secondary amines) with lithium diisopropylamide (LDA), diphenyl phosphorochloridate (DPPCl), and NaN3 yielded the corresponding alpha-azidobenzeneacetamides 6 in 45-50% yield (Schemes 2 and 3). In the case of Z-protected diisopropylamine 5b, the phosphate 7 was isolated as a minor product. A reaction mechanism for this unexpected transformation is proposed in Scheme 4, the key step being the ring closure of a benzylic anion to give an oxirane intermediate B. In cursory experiments, it was demonstrated that alpha-azidobenzeneacetamides 6 can be used as 2-phenylglycine synthons in the formation of dipeptides by using a phosphine-mediated coupling (Scheme 5 ) .

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:1997
Deposited On:18 Nov 2013 10:09
Last Modified:05 Apr 2016 17:09
Publisher:Wiley-Blackwell
ISSN:0018-019X
Funders:Swiss National Science Foundation, F. Hoffmann-La Roche AG, Basel
Publisher DOI:https://doi.org/10.1002/hlca.19970800706

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