Palladium-catalyzed stereoretentive olefination of unactivated C(sp3)-H bonds with vinyl iodides at room temperature: Synthesis of β-vinyl α-amino acids

Bo Wang; Chengxi Lu; Shu Yu Zhang; Gang He; William A. Nack; Gong Chen

doi:10.1021/ol503248f

Palladium-catalyzed stereoretentive olefination of unactivated C(sp³)-H bonds with vinyl iodides at room temperature: Synthesis of β-vinyl α-amino acids

Bo Wang, Chengxi Lu, Shu Yu Zhang, Gang He, William A. Nack, Gong Chen

Chemistry

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

85 Scopus citations

Abstract

A method is reported for palladium-catalyzed N-quinolyl carboxamide-directed olefination of the unactivated C(sp³)-H bonds of phthaloyl alanine with a broad range of vinyl iodides at room temperature. This reaction represents the first example of the stereoretentive installation of multisubstituted terminal and internal olefins onto unactivated C(sp³)-H bonds. These methods enable access to a wide range of challenging β-vinyl α-amino acid products in a streamlined and controllable fashion, beginning from simple precursors.

Original language	English (US)
Pages (from-to)	6260-6263
Number of pages	4
Journal	Organic Letters
Volume	16
Issue number	23
DOIs	https://doi.org/10.1021/ol503248f
State	Published - Dec 5 2014

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol503248f

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title = "Palladium-catalyzed stereoretentive olefination of unactivated C(sp3)-H bonds with vinyl iodides at room temperature: Synthesis of β-vinyl α-amino acids",

abstract = "A method is reported for palladium-catalyzed N-quinolyl carboxamide-directed olefination of the unactivated C(sp3)-H bonds of phthaloyl alanine with a broad range of vinyl iodides at room temperature. This reaction represents the first example of the stereoretentive installation of multisubstituted terminal and internal olefins onto unactivated C(sp3)-H bonds. These methods enable access to a wide range of challenging β-vinyl α-amino acid products in a streamlined and controllable fashion, beginning from simple precursors.",

author = "Bo Wang and Chengxi Lu and Zhang, {Shu Yu} and Gang He and Nack, {William A.} and Gong Chen",

note = "Publisher Copyright: {\textcopyright} 2014 American Chemical Society.",

year = "2014",

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doi = "10.1021/ol503248f",

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T2 - Synthesis of β-vinyl α-amino acids

AU - Wang, Bo

AU - Lu, Chengxi

AU - Zhang, Shu Yu

AU - He, Gang

AU - Nack, William A.

AU - Chen, Gong

PY - 2014/12/5

Y1 - 2014/12/5

N2 - A method is reported for palladium-catalyzed N-quinolyl carboxamide-directed olefination of the unactivated C(sp3)-H bonds of phthaloyl alanine with a broad range of vinyl iodides at room temperature. This reaction represents the first example of the stereoretentive installation of multisubstituted terminal and internal olefins onto unactivated C(sp3)-H bonds. These methods enable access to a wide range of challenging β-vinyl α-amino acid products in a streamlined and controllable fashion, beginning from simple precursors.

AB - A method is reported for palladium-catalyzed N-quinolyl carboxamide-directed olefination of the unactivated C(sp3)-H bonds of phthaloyl alanine with a broad range of vinyl iodides at room temperature. This reaction represents the first example of the stereoretentive installation of multisubstituted terminal and internal olefins onto unactivated C(sp3)-H bonds. These methods enable access to a wide range of challenging β-vinyl α-amino acid products in a streamlined and controllable fashion, beginning from simple precursors.

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Palladium-catalyzed stereoretentive olefination of unactivated C(sp³)-H bonds with vinyl iodides at room temperature: Synthesis of β-vinyl α-amino acids

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