Enantioselective Allylic C−H Oxidation of Terminal Olefins to Isochromans by Palladium(II)/Chiral Sulfoxide Catalysis

Stephen E. Ammann; Wei Liu; M. Christina White

doi:10.1002/anie.201603576

Enantioselective Allylic C−H Oxidation of Terminal Olefins to Isochromans by Palladium(II)/Chiral Sulfoxide Catalysis

Stephen E. Ammann, Wei Liu, M. Christina White

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

Abstract

The enantioselective synthesis of isochroman motifs has been accomplished by palladium(II)-catalyzed allylic C−H oxidation from terminal olefin precursors. Critical to the success of this goal was the development and utilization of a novel chiral aryl sulfoxide-oxazoline (ArSOX) ligand. The allylic C−H oxidation reaction proceeds with the broadest scope and highest levels of asymmetric induction reported to date (avg. 92 % ee, 13 examples with greater than 90 % ee).

Original language	English (US)
Pages (from-to)	9571-9575
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	55
Issue number	33
DOIs	https://doi.org/10.1002/anie.201603576
State	Published - Aug 8 2016

Keywords

C−H activation
S ligands
asymmetric catalysis
oxidation
palladium

ASJC Scopus subject areas

Catalysis
General Chemistry

Online availability

10.1002/anie.201603576

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abstract = "The enantioselective synthesis of isochroman motifs has been accomplished by palladium(II)-catalyzed allylic C−H oxidation from terminal olefin precursors. Critical to the success of this goal was the development and utilization of a novel chiral aryl sulfoxide-oxazoline (ArSOX) ligand. The allylic C−H oxidation reaction proceeds with the broadest scope and highest levels of asymmetric induction reported to date (avg. 92 % ee, 13 examples with greater than 90 % ee).",

keywords = "C−H activation, S ligands, asymmetric catalysis, oxidation, palladium",

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note = "Publisher Copyright: {\textcopyright} 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim",

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AU - Liu, Wei

AU - White, M. Christina

PY - 2016/8/8

Y1 - 2016/8/8

N2 - The enantioselective synthesis of isochroman motifs has been accomplished by palladium(II)-catalyzed allylic C−H oxidation from terminal olefin precursors. Critical to the success of this goal was the development and utilization of a novel chiral aryl sulfoxide-oxazoline (ArSOX) ligand. The allylic C−H oxidation reaction proceeds with the broadest scope and highest levels of asymmetric induction reported to date (avg. 92 % ee, 13 examples with greater than 90 % ee).

AB - The enantioselective synthesis of isochroman motifs has been accomplished by palladium(II)-catalyzed allylic C−H oxidation from terminal olefin precursors. Critical to the success of this goal was the development and utilization of a novel chiral aryl sulfoxide-oxazoline (ArSOX) ligand. The allylic C−H oxidation reaction proceeds with the broadest scope and highest levels of asymmetric induction reported to date (avg. 92 % ee, 13 examples with greater than 90 % ee).

KW - C−H activation

KW - S ligands

KW - asymmetric catalysis

KW - oxidation

KW - palladium

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JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

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Enantioselective Allylic C−H Oxidation of Terminal Olefins to Isochromans by Palladium(II)/Chiral Sulfoxide Catalysis

Abstract

Keywords

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