Palladium-Catalyzed Regio- and Enantioselective Synthesis of Allylic Amines Featuring Tetrasubstituted Tertiary Carbons

Aijie Cai; Wusheng Guo; Luis Martínez-Rodríguez; Arjan W. Kleij

doi:10.1021/jacs.6b08841

Palladium-Catalyzed Regio- and Enantioselective Synthesis of Allylic Amines Featuring Tetrasubstituted Tertiary Carbons

Aijie Cai
, Wusheng Guo
, Luis Martínez-Rodríguez
, Arjan W. Kleij

The Barcelona Institute of Science and Technology
ICREA

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

186 Scopus citations

Abstract

The first asymmetric synthesis of α,α-disubstituted allylic N-arylamines based on a palladium-catalyzed allylic amination has been developed. The protocol uses highly modular vinyl cyclic carbonates and unactivated aromatic amine nucleophiles as substrates. The catalytic process features minimal waste production, ample scope in reaction partners, high asymmetric induction up to 97% ee, and operational simplicity.

Original language	English
Pages (from-to)	14194-14197
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	138
Issue number	43
DOIs	https://doi.org/10.1021/jacs.6b08841
State	Published - 2 Nov 2016
Externally published	Yes

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abstract = "The first asymmetric synthesis of α,α-disubstituted allylic N-arylamines based on a palladium-catalyzed allylic amination has been developed. The protocol uses highly modular vinyl cyclic carbonates and unactivated aromatic amine nucleophiles as substrates. The catalytic process features minimal waste production, ample scope in reaction partners, high asymmetric induction up to 97\% ee, and operational simplicity.",

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AU - Kleij, Arjan W.

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AB - The first asymmetric synthesis of α,α-disubstituted allylic N-arylamines based on a palladium-catalyzed allylic amination has been developed. The protocol uses highly modular vinyl cyclic carbonates and unactivated aromatic amine nucleophiles as substrates. The catalytic process features minimal waste production, ample scope in reaction partners, high asymmetric induction up to 97% ee, and operational simplicity.

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Palladium-Catalyzed Regio- and Enantioselective Synthesis of Allylic Amines Featuring Tetrasubstituted Tertiary Carbons

Abstract

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