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Synfacts 2017; 13(01): 0045
DOI: 10.1055/s-0036-1589746
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Cyclohexenylamines and Cyclohexenols by Rhodium-Catalyzed Cycloaddition

Contributor(s):
Mark Lautens
,
Hyung Yoon
Masutomi K, Sugiyama H, Uekusa H, Shibata Y, Tanaka K * Tokyo Institute of Technology, Japan
Asymmetric Synthesis of Protected Cyclohexenylamines and Cyclohexenols by Rhodium-Catalyzed [2+2+2] Cycloaddition.

Angew. Chem. Int. Ed. 2016;
55: 15373-15376
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Publication History

Publication Date:
19 December 2016 (online)

 
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Key words

rhodium - [2+2+2] cycloaddition - cyclohexenylamines

Significance

Transition-metal-catalyzed [2+2+2] cycloadditions of diynes or enynes with unsaturated moieties have become an attractive method for the stereoselective construction of carbocycles. Herein, Tanaka and co-workers report a regiodivergent asymmetric rhodium-catalyzed [2+2+2] cycloaddition generating cyclohexenylamines and cyclohexenols.


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Comment

The rhodium-catalyzed [2+2+2] cyclo­addition of enynes bearing 1,1-disubstituted olefins provided the desired products in moderate to excellent yields and with excellent enantioselectivities. Interestingly, by employing enynes with monosubstituted olefins, a different regioisomer is reported to be formed in moderate yields and with excellent enantioselectivities.


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