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Synfacts 2008(4): 0422-0422  
DOI: 10.1055/s-2008-1042837
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York

Alternative Route to Aza-MBH Products

Contributor(s): Benjamin List, Corinna Reisinger
Y. Zhang, Y.-K. Liu, T.-R. Kang, Z.-K. Hu, Y.-C. Chen*
Sichuan University, Chengdu, P. R. of China
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Publication History

Publication Date:
19 March 2008 (online)

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Significance

The authors have developed an asymmetric Mannich-type reaction of stabilized phosphorus ylide 1 and both aromatic and aliphatic N-Boc-protected aldimines 2. The reaction is mediated by the readily available and recyclable chiral bisthiourea catalyst 3. Subsequent Wittig reaction of the Mannich products 5 with formaldehyde furnishes N-Boc-β-amino-α-methylene carboxylic esters 4 in good to high yields and enantio­selectivities.