Synthesis 2006(9): 1447-1460  
DOI: 10.1055/s-2006-926437
PAPER
© Georg Thieme Verlag Stuttgart · New York

Asymmetric Michael Additions of a Chiral Phosphite to Nitroalkenes and Knoevenagel Acceptors

Dieter Enders*, Livio Tedeschi, Dominik Förster
Institut für Organische Chemie, RWTH Aachen, Landoltweg 1, 52074 Aachen, Germany
Fax: +49(241)8092127; e-Mail: enders@rwth-aachen.de ;
Further Information

Publication History

Received 23 November 2005
Publication Date:
11 April 2006 (eFirst)

Abstract

The diastereoselective Michael addition of an enantiopure phosphite to nitroalkenes and α,β-unsaturated malonates is described. High asymmetric inductions were obtained using a readily available TADDOL auxiliary. Racemization-free cleavage of the auxiliary led to α-substituted β-nitro phosphonates and β-substituted β-phosphono malonates in good yields and high enantiomeric excesses, respectively. An extension of the method to the synthesis of α,β-disubstituted β-nitrophosphonates with two new neighboring stereogenic centers is also reported.

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18

The crystal structure of 8e has been deposited as supplementary publication no. CCDC-281444 at the Cambridge Crystallographic Data Centre. Copies of the data can be obtained free of charge on application to CCDC 12 Union Road Cambridge CB2 1EZ UK [fax: +44(1223) 336033; e-mail: deposit@ccdc.cam.ac.uk or
http//www.ccdc.cam.ac.uk].