Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 351, Issue 13, Pages 2096-2100Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.200900413
Keywords
alpha-amido sulfones; asymmetric synthesis; aza-Henry reaction; imines; rosin-derived thiourea
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Funding
- National Natural Science Foundation of China [20525206, 20772052, 20621091]
- Chang Jiang Program of the Ministry of Education of China
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The doubly stereocontrolled organocatalytic aza-Henry reaction of nitroalkanes to N-Bocimines generated in situ from a variety of substituted alpha-amido sulfones was investigated for the first time, in general, affording the corresponding products with high to excellent yields (up to 93% yield) and enantioselectivities (up to 98% ee), and satisfactory diastereoselectivies (anti/syn up to 98:2). Furthermore, these organocatalysts based on rosin have been proved to be the very effective promoters for this catalytic asymmetric process along side the Cinchona alkaloid-derived catalysts.
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