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Synfacts 2008(9): 0988-0988  
DOI: 10.1055/s-2008-1078665
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

Highly anti-Selective Asymmetric Nitro-Mannich Reactions

Contributor(s): Benjamin List, Steffen Müller
C.-J. Wang*, X.-Q. Dong, Z.-H. Zhang, Z.-Y. Xue, H.-L- Teng
Wuhan University,P. R. of China
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Publication History

Publication Date:
22 August 2008 (online)

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Significance

The authors report a highly diastereoselective and enantioselective reaction of N-Boc-imines 1 with nitroalkanes 2 in the presence of catalyst 3. Aromatic, heteroaromatic and aliphatic imines were converted into the corresponding products 4 in excellent yields (88-99%) and outstanding enantioselectivities (er = 98:2 up to 99.5:0.5) for the highly favored anti-diastereo­mer (dr = 93:7 to 99:1). The free NH group of the sulfonamide functionality turned out to be essential for the performance of the multi-hydrogen-bonding catalyst.