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  • Enantioselective and solvent-controlled diastereoselective Mannich reaction of isatin imines with hydroxyacetone: synthesis of 3-substituted 3-aminooxindoles.

Enantioselective and solvent-controlled diastereoselective Mannich reaction of isatin imines with hydroxyacetone: synthesis of 3-substituted 3-aminooxindoles.

The Journal of organic chemistry (2012-03-02)
Qi-Xiang Guo, Yu-Wan Liu, Xing-Cheng Li, Ling-Zhi Zhong, Yun-Gui Peng
ABSTRACT

The diastereoselectively switchable enantioselective Mannich reaction of isatin imines with hydroxyacetone is reported. The chiral primary amino acid catalyzed this Mannich reaction to afford both anti- and syn-Mannich adducts in high yields, good diastereoselectivities, and enantioselectivities. The reason for the solvent control of the diastereoselectivity phenomenon was investigated.

MATERIALS
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Product Description

Sigma-Aldrich
Hydroxyacetone, contains ≤500 ppm sodium carbonate as stabilizer, technical grade, 90%