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Issue 79, 2012
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Chemo- and enantioselective Rh-catalysed hydrogenation of 3-methylene-1,2-diazetidines: application to vicinal diamine synthesis

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Abstract

Rhodium catalysed hydrogenation of 3-methylene-1,2-diazetidines with a range of chiral ligands is reported. Using Mandyphos, excellent levels of chemo- and enantioselectivity (up to 89% ee) can be achieved. Reductive cleavage of the derived 3-substituted 1,2-diazetidine with LiDBB provides the enantioenriched biscarbamate protected 1,2-diamine.

Graphical abstract: Chemo- and enantioselective Rh-catalysed hydrogenation of 3-methylene-1,2-diazetidines: application to vicinal diamine synthesis

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Supplementary files

Article information


Submitted
27 Jul 2012
Accepted
17 Aug 2012
First published
20 Aug 2012

Chem. Commun., 2012,48, 9852-9854
Article type
Communication

Chemo- and enantioselective Rh-catalysed hydrogenation of 3-methylene-1,2-diazetidines: application to vicinal diamine synthesis

G. P. Iacobini, D. W. Porter and M. Shipman, Chem. Commun., 2012, 48, 9852 DOI: 10.1039/C2CC35445D

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