Enantioselective Functionalization of Enamides at the β-Carbon Center with Indoles

Mirza A. Saputra; Binod Nepal; Nitin S. Dange; Pu Du; Frank R. Fronczek; Revati Kumar; Rendy Kartika

doi:10.1002/anie.201808764

Enantioselective Functionalization of Enamides at the β-Carbon Center with Indoles

Mirza A. Saputra, Binod Nepal, Nitin S. Dange, Pu Du, Frank R. Fronczek, Revati Kumar, Rendy Kartika

Research output: Contribution to journal › Article › peer-review

8 Citations (Scopus)

Abstract

We report an enantioconvergent approach for the functionalization of enamides at the β-carbon atom, which involves a chiral Brønsted acid induced tautomerization of 2-amidoallyl into 1-amidoallyl cations. These putative reactive intermediates were produced by ionization of racemic α-hydroxy enamides with a chiral Brønsted acid and captured with substituted indoles in a highly regio- and enantioselective manner.

Original language	English
Pages (from-to)	15558-15562
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	57
Issue number	47
DOIs	https://doi.org/10.1002/anie.201808764
Publication status	Published - 19 Nov 2018

Keywords

2-amidoallyl cations
asymmetric catalysis
Brønsted acids
indoles
tautomerization

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title = "Enantioselective Functionalization of Enamides at the β-Carbon Center with Indoles",

abstract = "We report an enantioconvergent approach for the functionalization of enamides at the β-carbon atom, which involves a chiral Br{\o}nsted acid induced tautomerization of 2-amidoallyl into 1-amidoallyl cations. These putative reactive intermediates were produced by ionization of racemic α-hydroxy enamides with a chiral Br{\o}nsted acid and captured with substituted indoles in a highly regio- and enantioselective manner.",

keywords = "2-amidoallyl cations, asymmetric catalysis, Br{\o}nsted acids, indoles, tautomerization",

author = "Saputra, {Mirza A.} and Binod Nepal and Dange, {Nitin S.} and Pu Du and Fronczek, {Frank R.} and Revati Kumar and Rendy Kartika",

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T1 - Enantioselective Functionalization of Enamides at the β-Carbon Center with Indoles

AU - Saputra, Mirza A.

AU - Nepal, Binod

AU - Dange, Nitin S.

AU - Du, Pu

AU - Fronczek, Frank R.

AU - Kumar, Revati

AU - Kartika, Rendy

PY - 2018/11/19

Y1 - 2018/11/19

N2 - We report an enantioconvergent approach for the functionalization of enamides at the β-carbon atom, which involves a chiral Brønsted acid induced tautomerization of 2-amidoallyl into 1-amidoallyl cations. These putative reactive intermediates were produced by ionization of racemic α-hydroxy enamides with a chiral Brønsted acid and captured with substituted indoles in a highly regio- and enantioselective manner.

AB - We report an enantioconvergent approach for the functionalization of enamides at the β-carbon atom, which involves a chiral Brønsted acid induced tautomerization of 2-amidoallyl into 1-amidoallyl cations. These putative reactive intermediates were produced by ionization of racemic α-hydroxy enamides with a chiral Brønsted acid and captured with substituted indoles in a highly regio- and enantioselective manner.

KW - 2-amidoallyl cations

KW - asymmetric catalysis

KW - Brønsted acids

KW - indoles

KW - tautomerization

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SN - 1433-7851

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JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 47

ER -

Enantioselective Functionalization of Enamides at the β-Carbon Center with Indoles

Abstract

Keywords

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