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Synfacts 2015; 11(1): 0063
DOI: 10.1055/s-0034-1379746
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Intramolecular Asymmetric Desymmetrization via Copper Catalysis

Contributor(s):
Hisashi Yamamoto
,
Sukalyan Bhadra
Wu X.-P, Su Y, Gu P * Ningxia University, Yinchuan and Lanzhou University, P. R. of China
Catalytic Enantioselective Desymmetrization of 1,3-Diazido-2-propanol via Intramolecular Interception of Alkyl Azides with Diazo(aryl)acetates.

Org. Lett. 2014;
16: 5339-5341
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Publication History

Publication Date:
15 December 2014 (online)

 
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Key words

asymmetric desymmetrization - alkyl azides - bisoxazolines - copper

Significance

Hydroxy- and amino-functionalized C3-fragments play a pivotal role as synthetic intermediates. Whereas enantioselective desymmetrization of diols and glycerol were developed to ­provide hydroxyl-containing C3-fragments, the corresponding preparation of amino-containing C3-fragments has been rarely documented. Herein, Gu and co-workers present the asymmetric desymmetrization of 1,3-diazido-2-propanols catalyzed by copper–PhBox.


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Comment

The title transformation is enabled in an enantioselective fashion by CuPF6(MeCN)4 in the presence of (S,S)-PhBox and NaBARF with the larger and non-coordinating BARF– anion. The new method provides reliable access to enantioenriched azido-substituted 5,6-dihydro-1,4-oxazin-2-ones, which can be further converted into useful N-containing scaffolds.


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