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Synthesis 2011(21): 3475-3481  
DOI: 10.1055/s-0030-1260244
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Mild One-Pot Conversion of Alkenes into Amines through Tandem Ozonolysis and Reductive Amination

ShivaKumar Kyasa, Thomas J. Fisher, Patrick H. Dussault*
Department of Chemistry, University of Nebraska-Lincoln, Lincoln, NE 68588-0304, USA
Fax: +1(402)4729402; e-Mail: pdussault1@unl.edu;
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Publikationsverlauf

Received 30 June 2011
Publikationsdatum:
27. September 2011 (online)

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Abstract

The selective reduction of hydroperoxyacetals to aldehydes by sodium triacetoxyborohydride provides the basis for a mild one-pot synthesis of amines from alkenes.

Key words

ozonolysis - hydroperoxyacetal - reductive amination - amine - sodium triacetoxyborohydride

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1

These authors contributed equally to this manuscript.

15

All products were purified by flash chromatography to greater than 95% purity (NMR). Hydroperoxides were characterized by ¹H/¹³C NMR; aldehydes and amines were characterized by ¹H/¹³C NMR, IR, and HRMS.