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Synfacts 2011(12): 1359-1359  
DOI: 10.1055/s-0031-1289370
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

Friedel-Crafts Alkylation, Internal Redox Reaction, and Umpolung Cascade

Contributor(s): Benjamin List, Ilija Čorić
Y. Sohtome*, T. Yamaguchi, B. Shin, K. Nagasawa*
Tokyo University of Agriculture and Technology, Japan
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Publication History

Publication Date:
18 November 2011 (online)

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Significance

The stereoselective synthesis of N,N-bis(dihydrofuranyl)hydroxyamines 4 from phenols 2 and nitroolefins 3 has been reported. A combination of guanidine/bisthiourea organocatalyst 1 and potassium carbonate as base gave the products with excellent enantioselectivity and good yields. The role of the proposed intermediate 6 during the cascade was supported by the formation of 7 in a reaction of isolated 5a with nitro­sobenzene.