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A highly enantioselective cis-hydrogenation of 2,3,4-trisubstituted quinolines has been realized for the first time using chiral borane catalysts generated in situ from chiral dienes. A variety of tetrahydroquinoline derivatives containing three contiguous stereogenic centers were obtained in 76-99% yields with 82-99% ee's.
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Zhang et al. (2015) studied this question.
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