Highly enantioselective pictet-spengler reactions with α-ketoamide- derived ketimines: Access to an unusual class of quaternary α-amino amides

Angewandte Chemie - International Edition

Volumn 48, Issue 13, 2009, Pages 2403-2406

  Bou Hamdan, Farhan R ^a   Leighton, James L ^a  

^a Columbia University ^*  (United States)

Author keywords

Asymmetric synthesis; Heterocycles; Ketimines; Lewis acids; Pictet Spengler reaction

Indexed keywords

AMIDES;

ASYMMETRIC SYNTHESIS; HETEROCYCLES; KETIMINES; LEWIS ACID; PICTET-SPENGLER REACTIONS;

ENANTIOSELECTIVITY;

AMIDE; AMINO ACID; HETEROCYCLIC COMPOUND; SILANE DERIVATIVE;

CATALYSIS; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

AMIDES; AMINO ACIDS; CATALYSIS; HETEROCYCLIC COMPOUNDS; SILANES; STEREOISOMERISM;

EID: 70349783579     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200806110     Document Type: Article

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36. On this scale (0.15 mmol), reactions run with lowered silane loadingsoften proceeded with loss in enantioselectivity. We attribute this outcome to aBrønsted acid catalyzed reaction, likely owing to trace moisture.
37. On this larger scale, the problem described in Ref. [10] is mitigated,and the silane loading may be lowered with no loss in enantioselectivity.
38. Full details are provided in the Supporting Information file.