Asymmetric Strecker Reaction of Ketoimines Catalyzed by a Novel Chiral Bifunctional N,N′-Dioxide

Asymmetric Strecker Reaction of Ketoimines Catalyzed by a Novel Chiral Bifunctional N,N′-Dioxide

A novel bifunctional N,N′‐dioxide derived from L‐prolinamide was employed to catalyze the enantioselective Strecker reaction of a range of N‐tosyl ketoimines, and an effective additive was used to improve the reactivity (up to 99 % yield) as well as the enantioselectivity (up to 91 % ee). In additio...

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Veröffentlicht in:Advanced synthesis & catalysis 2006-12, Vol.348 (18), p.2579-2584
Hauptverfasser: Huang, Xiao, Huang, Jinglun, Wen, Yuehong, Feng, Xiaoming
Format: Artikel
Sprache:eng
Schlagworte:
asymmetric catalysis
ketoimines
organocatalyst
Strecker reaction
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Zusammenfassung:A novel bifunctional N,N′‐dioxide derived from L‐prolinamide was employed to catalyze the enantioselective Strecker reaction of a range of N‐tosyl ketoimines, and an effective additive was used to improve the reactivity (up to 99 % yield) as well as the enantioselectivity (up to 91 % ee). In addition, a rational transition state was proposed to elucidate the origin of chiral induction in which an S‐adduct was produced.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.200600238