Chemistry Letters
Online ISSN : 1348-0715
Print ISSN : 0366-7022
ISSN-L : 0366-7022
Letter
Organocatalytic Asymmetric Synthesis of N,N-Bis(dihydrofuranyl)hydroxyamines: A Cascade Reaction Involving Friedel–Crafts Alkylation, Internal Redox Reaction, and Umpolung
Yoshihiro SohtomeTakahisa YamaguchiBongki ShinKazuo Nagasawa
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2011 Volume 40 Issue 8 Pages 843-845

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Abstract

Stereoselective syntheses of N,N-bis(dihydrofuranyl)hydroxyamines from phenols and nitroolefins have been accomplished by means of cycle-specific catalysis with guanidine/bisthiourea organocatalyst and achiral base. Circumstantial evidence supports the idea that a nitroso intermediate participates in the dimerization, which involves internal redox reaction/umpolung.

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© 2011 The Chemical Society of Japan
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