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Synfacts 2016; 12(07): 0693
DOI: 10.1055/s-0035-1562292
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Gd-Catalyzed Photocycloaddition of Aryl Cyclopropyl Ketones to Alkenes

Contributor(s):
Hisashi Yamamoto
,
Masahiro Sai
Amador AG, Sherbrook EM, Yoon TP * University of Wisconsin–Madison, USA
Enantioselective Photocatalytic [3+2] Cycloadditions of Aryl Cyclopropyl Ketones.

J. Am. Chem. Soc. 2016;
138: 4722-4725
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Further Information

Publication History

Publication Date:
17 June 2016 (online)

 
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Key words

cycloaddition - photoredox reaction - gadolinium catalysis

Significance

The authors report a gadolinium-catalyzed asymmetric [3+2] photocycloaddition of aryl cyclopropyl ketones with alkenes. A variety of chiral cyclopentanes were obtained in high yields (≤95%) and stereoselectivities (up to >99% ee and dr up to >20:1).


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Comment

This result demonstrates that a combination of a chiral Lewis acid and photoredox catalysis offers a robust and potentially general approach to photochemical stereocontrol that is broadly applicable to the increasing number of powerful transformations achievable by using photoredox catalysis.


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