Conjugate-Base-Stabilized Brønsted Acids: Catalytic Enantioselective Pictet–Spengler Reactions with Unmodified Tryptamine

Conjugate-Base-Stabilized Brønsted Acids: Catalytic Enantioselective Pictet–Spengler Reactions with Unmodified Tryptamine

A conjugate-base-stabilized Brønsted acid facilitates catalytic enantioselective Pictet–Spengler reactions with unmodified tryptamine. The chiral carboxylic acid catalyst is readily assembled in just two steps and enables the formation of β-carbolines with up to 92% ee. Achiral acid additives or in...

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Veröffentlicht in:Organic letters 2014-02, Vol.16 (3), p.1012-1015
Hauptverfasser: Mittal, Nisha, Sun, Diana X, Seidel, Daniel
Format: Artikel
Sprache:eng
Schlagworte:
Carbolines - chemistry
Carboxylic Acids - chemistry
Catalysis
Molecular Structure
Stereoisomerism
Tryptamines - chemistry
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Zusammenfassung:A conjugate-base-stabilized Brønsted acid facilitates catalytic enantioselective Pictet–Spengler reactions with unmodified tryptamine. The chiral carboxylic acid catalyst is readily assembled in just two steps and enables the formation of β-carbolines with up to 92% ee. Achiral acid additives or in situ Boc-protection facilitate catalyst turnover.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol403773a