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Synfacts 2016; 12(1): 0041
DOI: 10.1055/s-0035-1561044
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Asymmetric Rhodium-Catalyzed C–C Activation of Cyclobutanones

Contributor(s):
Mark Lautens
,
Charles C. J. Loh
Zhou X, Dong G * University of Texas at Austin, USA
[4+1] vs [4+2]: Catalytic Intramolecular Coupling between Cyclobutanones and Trisubstituted Allenes via C–C Activation.

J. Am. Chem. Soc. 2015;
137: 13715-13721
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Further Information

Publication History

Publication Date:
16 December 2015 (online)

 
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Key words

rhodium catalysis - [4+1] cyclization - enantioselective reaction

Significance

C–C activation is an attractive method to functionalize strained four-membered ring systems. Zhou and Dong demonstrate the utility of allenes as a formal vinyl carbenoid in a rhodium-catalyzed asymmetric intramolecular ring expansion of cyclobutanones.


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Comment

An impressive substrate scope for this C–C activation protocol is demonstrated. Challenging cyclobutanone substrates such as those that are α-substituted also worked for this methodology, albeit with slightly diminished yields.


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