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Sequential allylic C-H amination/vinylic C-H arylation: a strategy for unnatural amino acid synthesis from ?-olefins.

ABSTRACT: Tandem reaction sequences that selectively convert multiple C-H bonds of abundant hydrocarbon feedstocks to functionalized materials enable rapid buildup of molecular complexity in an economical way. A tandem C-H amination/vinylic C-H arylation reaction sequence is described under Pd(II)/sulfoxide-catalysis that furnishes a wide range of ?- and ?-homophenylalanine precursors from commodity ?-olefins and readily available aryl boronic acids. General routes to enantiopure amino acid esters and densely functionalized homophenylalanine derivatives are demonstrated.

SUBMITTER: Jiang C

PROVIDER: S-EPMC4104998 | biostudies-literature | 2012 Mar

REPOSITORIES: biostudies-literature

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Sequential allylic C-H amination/vinylic C-H arylation: a strategy for unnatural amino acid synthesis from α-olefins.

Jiang Chao C Covell Dustin J DJ Stepan Antonia F AF Plummer Mark S MS White M Christina MC

Organic letters 20120224 6

Tandem reaction sequences that selectively convert multiple C-H bonds of abundant hydrocarbon feedstocks to functionalized materials enable rapid buildup of molecular complexity in an economical way. A tandem C-H amination/vinylic C-H arylation reaction sequence is described under Pd(II)/sulfoxide-catalysis that furnishes a wide range of α- and β-homophenylalanine precursors from commodity α-olefins and readily available aryl boronic acids. General routes to enantiopure amino acid esters and den ...[more]

PMID: 22360547

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