Carbonyl catalysis enables a biomimetic asymmetric Mannich reaction
Keyword(s):
Chiral amines are widely used as catalysts in asymmetric synthesis to activate carbonyl groups for α-functionalization. Carbonyl catalysis reverses that strategy by using a carbonyl group to activate a primary amine. Inspired by biological carbonyl catalysis, which is exemplified by reactions of pyridoxal-dependent enzymes, we developed an N-quaternized pyridoxal catalyst for the asymmetric Mannich reaction of glycinate with aryl N-diphenylphosphinyl imines. The catalyst exhibits high activity and stereoselectivity, likely enabled by enzyme-like cooperative bifunctional activation of the substrates. Our work demonstrates the catalytic utility of the pyridoxal moiety in asymmetric catalysis.
Keyword(s):
2006 ◽
Vol 71
(11)
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pp. 4222-4226
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2004 ◽
Vol 101
(16)
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pp. 5776-5781
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Keyword(s):
2018 ◽
Vol 16
(5)
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pp. 771-779
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