Issue 6, 2012
From the journal:

Chemical Science

Catalytic asymmetric α-amination of carboxylic acids using isothioureas†

Louis C. Morrill,a   Tomas Lebl,a   Alexandra M. Z. Slawina  and  Andrew D. Smith*a  

* Corresponding authors

a EaStCHEM, School of Chemistry, University of St Andrews, North Haugh, St Andrews, UK
E-mail: ads10@st-andrews.ac.uk

Abstract

HBTM-2.1 promotes the direct asymmetric α-amination of carboxylic acids with N-aryl-N-aroyldiazenes at low catalyst loadings (as low as 0.25 mol%), giving either 1,3,4-oxadiazin-6-ones or N-protected α-amino acid derivatives (upon ring opening) with exquisite enantiocontrol (typically ≥99% ee).

Graphical abstract: Catalytic asymmetric α-amination of carboxylic acids using isothioureas

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Article information

DOI
https://doi.org/10.1039/C2SC20171B
Article type
Edge Article
Submitted
09 Feb 2012
Accepted
07 Mar 2012
First published
08 Mar 2012

Chem. Sci., 2012,3, 2088-2093

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Catalytic asymmetric α-amination of carboxylic acids using isothioureas

L. C. Morrill, T. Lebl, A. M. Z. Slawin and A. D. Smith, Chem. Sci., 2012, 3, 2088 DOI: 10.1039/C2SC20171B

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