Please use this identifier to cite or link to this item:
Title: Unusual Reactivity of Nitronates with an Aryl Alkyl Carbonate: Synthesis of alpha-Amino Esters
Authors: Reddy, Golipalli Ramana
Mukherjee, Debopreeti
Chittoory, Arjun Kumar
Rajaram, Sridhar
Keywords: Organic Chemistry
Radical Conjugate Additions
Catalytic Asymmetric-Synthesis
Phase-Transfer Catalysis
Ambident Reactivity
Nitrile Oxides
Issue Date: 2014
Publisher: American Chemical Society
Citation: Reddy, GR; Mukherjee, D; Chittoory, AK; Rajaram, S, Unusual Reactivity of Nitronates with an Aryl Alkyl Carbonate: Synthesis of alpha-Amino Esters. Organic Letters 2014, 16 (22) 5874-5877,
Organic Letters
Abstract: The monoanions of nitroalkanes are ambident nucleophiles that react with carbonate electrophiles through the oxygen atom. Products arising from reactivity at the carbon atom will yield alpha-nitro esters, which are precursors for alpha-amino esters. We demonstrate this in the reactions of nitroalkanes with benzyl phenyl carbonate and DABCO where alpha-nitro esters are obtained instead of nitrile oxides. The products are readily reduced to alpha-amino esters. This pathway could be a safe alternative to the Strecker reaction.
Description: Restricted Access
ISSN: 1523-7060
Appears in Collections:Research Articles (Sridhar Rajaram)

Files in This Item:
File Description SizeFormat 
  Restricted Access
537.43 kBAdobe PDFView/Open Request a copy

Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.