Direct Visible-Light-Excited Asymmetric Lewis Acid Catalysis of Intermolecular [2+2] Photocycloadditions

Xiaoqiang Huang; Taylor R. Quinn; Klaus Harms; Richard D. Webster; Lilu Zhang; Olaf Wiest; Eric Meggers

doi:10.1021/jacs.7b04363

Direct Visible-Light-Excited Asymmetric Lewis Acid Catalysis of Intermolecular [2+2] Photocycloadditions

Xiaoqiang Huang, Taylor R. Quinn, Klaus Harms, Richard D. Webster, Lilu Zhang, Olaf Wiest, Eric Meggers^*

^*Corresponding author for this work

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

206 Citations (Scopus)

Abstract

A reaction design is reported in which a substrate-bound chiral Lewis acid complex absorbs visible light and generates an excited state that directly reacts with a cosubstrate in a highly stereocontrolled fashion. Specifically, a chiral rhodium complex catalyzes visible-light-activated intermolecular [2+2] cycloadditions, providing a wide range of cyclobutanes with up to >99% ee and up to >20:1 d.r. Noteworthy is the ability to create vicinal all-carbon-quaternary stereocenters including spiro centers in an intermolecular fashion.

Original language	English
Pages (from-to)	9120-9123
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	139
Issue number	27
DOIs	https://doi.org/10.1021/jacs.7b04363
Publication status	Published - Jul 12 2017
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2017 American Chemical Society.

ASJC Scopus Subject Areas

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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10.1021/jacs.7b04363

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title = "Direct Visible-Light-Excited Asymmetric Lewis Acid Catalysis of Intermolecular [2+2] Photocycloadditions",

abstract = "A reaction design is reported in which a substrate-bound chiral Lewis acid complex absorbs visible light and generates an excited state that directly reacts with a cosubstrate in a highly stereocontrolled fashion. Specifically, a chiral rhodium complex catalyzes visible-light-activated intermolecular [2+2] cycloadditions, providing a wide range of cyclobutanes with up to >99% ee and up to >20:1 d.r. Noteworthy is the ability to create vicinal all-carbon-quaternary stereocenters including spiro centers in an intermolecular fashion.",

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AU - Quinn, Taylor R.

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AU - Webster, Richard D.

AU - Zhang, Lilu

AU - Wiest, Olaf

AU - Meggers, Eric

PY - 2017/7/12

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AB - A reaction design is reported in which a substrate-bound chiral Lewis acid complex absorbs visible light and generates an excited state that directly reacts with a cosubstrate in a highly stereocontrolled fashion. Specifically, a chiral rhodium complex catalyzes visible-light-activated intermolecular [2+2] cycloadditions, providing a wide range of cyclobutanes with up to >99% ee and up to >20:1 d.r. Noteworthy is the ability to create vicinal all-carbon-quaternary stereocenters including spiro centers in an intermolecular fashion.

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Direct Visible-Light-Excited Asymmetric Lewis Acid Catalysis of Intermolecular [2+2] Photocycloadditions

Abstract

Bibliographical note

ASJC Scopus Subject Areas

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