Regioselective Functionalization of Enamides at the α-Carbon via Unsymmetrical 2-Amidoallyl Cations

Mirza A. Saputra; Nitin S. Dange; Alexander H. Cleveland; Joshua A. Malone; Frank R. Fronczek; Rendy Kartika

doi:10.1021/acs.orglett.7b00962

Regioselective Functionalization of Enamides at the α-Carbon via Unsymmetrical 2-Amidoallyl Cations

Mirza A. Saputra, Nitin S. Dange, Alexander H. Cleveland, Joshua A. Malone, Frank R. Fronczek, Rendy Kartika

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

11 Citations (Scopus)

Abstract

A new method to functionalize enamides via an intermediacy of unsymmetrical 2-amidoallyl cations is reported. Generated under mild Brønsted acid catalysis, these reactive species were found to undergo addition with various nucleophiles at the less substituted α-carbon to produce highly substituted enamides in high yields with complete control of regioselectivity.

Original language	English
Pages (from-to)	2414-2417
Number of pages	4
Journal	Organic Letters
Volume	19
Issue number	9
DOIs	https://doi.org/10.1021/acs.orglett.7b00962
Publication status	Published - 5 May 2017

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title = "Regioselective Functionalization of Enamides at the α-Carbon via Unsymmetrical 2-Amidoallyl Cations",

abstract = "A new method to functionalize enamides via an intermediacy of unsymmetrical 2-amidoallyl cations is reported. Generated under mild Br{\o}nsted acid catalysis, these reactive species were found to undergo addition with various nucleophiles at the less substituted α-carbon to produce highly substituted enamides in high yields with complete control of regioselectivity.",

author = "Saputra, {Mirza A.} and Dange, {Nitin S.} and Cleveland, {Alexander H.} and Malone, {Joshua A.} and Fronczek, {Frank R.} and Rendy Kartika",

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T1 - Regioselective Functionalization of Enamides at the α-Carbon via Unsymmetrical 2-Amidoallyl Cations

AU - Saputra, Mirza A.

AU - Dange, Nitin S.

AU - Cleveland, Alexander H.

AU - Malone, Joshua A.

AU - Fronczek, Frank R.

AU - Kartika, Rendy

PY - 2017/5/5

Y1 - 2017/5/5

N2 - A new method to functionalize enamides via an intermediacy of unsymmetrical 2-amidoallyl cations is reported. Generated under mild Brønsted acid catalysis, these reactive species were found to undergo addition with various nucleophiles at the less substituted α-carbon to produce highly substituted enamides in high yields with complete control of regioselectivity.

AB - A new method to functionalize enamides via an intermediacy of unsymmetrical 2-amidoallyl cations is reported. Generated under mild Brønsted acid catalysis, these reactive species were found to undergo addition with various nucleophiles at the less substituted α-carbon to produce highly substituted enamides in high yields with complete control of regioselectivity.

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DO - 10.1021/acs.orglett.7b00962

M3 - Article

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AN - SCOPUS:85019034583

SN - 1523-7060

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EP - 2417

JO - Organic Letters

JF - Organic Letters

IS - 9

ER -

Regioselective Functionalization of Enamides at the α-Carbon via Unsymmetrical 2-Amidoallyl Cations

Abstract

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