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Synfacts 2015; 11(1): 0089
DOI: 10.1055/s-0034-1379623
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Dearomatization of Indoles

Contributor(s):
Benjamin List
,
Lisa Kötzner
Romano C, Jia M, Monari M, Manoni E, Bandini M * University of Bologna, Italy
Metal-Free Enantioselective Electrophilic Activation of Allenamides: Stereoselective Dearomatization of Indoles.

Angew. Chem. Int. Ed. 2014;
53: 13854-13857
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Further Information

Publication History

Publication Date:
15 December 2014 (online)

 
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Key words

allenamides - dearomatization - quaternary carbon centers

Significance

Bandini and co-workers report an enantioselective dearomatization of indoles. Using 1 to 10 mol% of chiral phosphoric acid catalyst 1, the desired 3,3-disubstituted indolenines are obtained in moderate to high yields and good to excellent enantioselectivities.


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Comment

The authors developed an enantioselective electrophilic activation of allenamides, generating enantioenriched dearomatized 3,3-disubstituted indolenines as products. Additionally, a dearomatization–hydrogen transfer cascade was conducted. Performing the reaction in the presence of molecular sieves and Hantzsch ester, the corresponding indolines are obtained in good yields and with high diastereo- and enantioselectivities.


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