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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description	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.
doi_str_mv	10.1021/ol403773a
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subjects	Carbolines - chemistry Carboxylic Acids - chemistry Catalysis Molecular Structure Stereoisomerism Tryptamines - chemistry
title	Conjugate-Base-Stabilized Brønsted Acids: Catalytic Enantioselective Pictet–Spengler Reactions with Unmodified Tryptamine
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