Journal
ORGANIC CHEMISTRY FRONTIERS
Volume 7, Issue 17, Pages 2505-2510Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c9qo01304k
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- Ministry of Science and Technology of Taiwan (MOST)
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Chemoselective enantiodivergent reduction ofN-benzyl-alpha-keto amides catalyzed by chiral oxido-vanadium(v) complexes derived from a reduced form ofN-salicylidenel-tertleucinate can be achieved with good yields and good to high enantioselectivities. These chiral complexes were utilized in catalyzing the enantioselective synthesis of (R)-N-benzyl-mandelamide with pinacolborane and (S)-N-benzyl-mandelamide with catecholborane from the corresponding ketone precursors. A series of 12 different solvents and 8 different reducing agents were examined. By the use of pinacolborane (Risomer, 74-99% ee) or catecholborane (Sisomer, 60-90% ee), a handy approach for complementary asymmetric reduction of alpha-keto amides can be attained.
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