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A highly enantioselective Mannich reaction of α-fluoroindanones with isatin-derived N-Boc-ketimines catalyzed by a quinine-derived phase-transfer catalyst was developed. A variety of 3-substituted 3-amino-2-oxindoles bearing fluorine-containing, vicinal, tetrasubstituted stereocenters were constructed using this protocol in high yields (83–95%), with moderate to excellent enantioselectivities (66–91%) and high diastereoselectivities (up to >99:1).
Zhao et al. (Wed,) studied this question.