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Synlett 2009(5): 716-719  
DOI: 10.1055/s-0028-1087815
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Thieme Chemistry Journal Awardees - Where are They Now? Dibutyltin Dimethoxide Catalyzed N-Nitrosoaldol Reaction of Alkenyl Trichloroacetate

Akira Yanagisawa*a, Youhei Izumib, Satoshi Takeshitaa
a Department of Chemistry, Graduate School of Science, Chiba University, Inage, Chiba 263-8522, Japan
Fax: +81(43)2902789; e-Mail: ayanagi@faculty.chiba-u.jp;
b Graduate School of Science and Technology, Chiba University, Inage, Chiba 263-8522, Japan
Further Information

Publication History

Received 22 September 2008
Publication Date:
16 February 2009 (online)

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Abstract

Nitrosoaldol reaction between alkenyl trichloroacetates and nitrosobenzene has been achieved using dibutyltin dimethoxide as a catalyst, which is regenerated in the presence of methanol. The corresponding α-hydroxyamino ketones (N-adducts) have exclusively formed not only from cyclic alkenyl trichloroacetates but also from acyclic ones.

Key words

tin catalyst - nitrosoaldol reaction - α-hydroxyamino ketone - alkenyl trichloroacetate - nitrosobenzene

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