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Synfacts 2014; 10(1): 0048
DOI: 10.1055/s-0033-1340432
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Consecutive Intramolecular Desymmetrization and Kinetic Resolution

Contributor(s):
Hisashi Yamamoto
,
Atsuto Izumiseki
You YS, Kim TW, Kang SH * Korea Advanced Institute of Science and Technology, Daejeon, Korea
Asymmetric Formation of tert-Alkylamines from Serinols by a Dual Function Catalyst.

Chem. Commun. 2013;
49: 9669-9671
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Publication History

Publication Date:
13 December 2013 (online)

 
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Key words

copper - desymmetrization - kinetic resolution

Significance

This paper describes the consecutive intramolecular desymmetrization and kinetic resolution of 2-substituted N-phenoxycarbonylserinols by using bisoxazoline-CuCl2. The reaction products are obtained in good yield and excellent enantioselectivities (94–99% ee).


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Comment

The authors developed a unique asymmetric catalysis system using a single chiral Lewis acid catalyst, which steers two consecutive asymmetric reactions of intramolecular desymmetrization and kinetic resolution. The two successive chemical conversions became unusually ­enantioselective, resulting in the production of the oxazolidinone benzoates with excellent enantioselectivities, which signifies a powerful and synergistic dual function catalyst effect by a chiral catalyst.


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