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Synfacts 2014; 10(1): 0045
DOI: 10.1055/s-0033-1340433
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Rh2(R-TPCP)4-Catalyzed Enantioselective Syntheses of 2,5-Dihydroisoxazoles

Contributor(s):
Hisashi Yamamoto
,
Biplab Maji
Qin C, Davies HM. L * Emory University, Atlanta, USA
Rh2(R-TPCP)4-Catalyzed Enantioselective [3+2] Cycloaddition between Nitrones and Vinyldiazoacetates.

J. Am. Chem. Soc. 2013;
135: 14516-14519
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Publication History

Publication Date:
13 December 2013 (online)

 
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Key words

[3+2] cycloaddition - nitrones - vinyldiazoacetates

Significance

Exploring the vinylogous reactivity of vinyl rhodium carbenoids, the authors report the Rh2(R-TPCP)4-catalyzed enantioselective formal [3+2] cycloaddition between nitrones and vinyldiazoacetates. With only 2 mol% of the bulky rhodium catalyst, the 2,5-dihydroisoxazoles were obtained in good yields and moderate to excellent enantioselectivities.


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Comment

Doyle and colleagues previously reported a dirhodium complex catalyzed synthesis of 3,6-dihydro-1,2-oxazines via an asymmetric formal [3+3] cycloaddition between nitrones and vinyldiazo compounds (J. Am. Chem. Soc. 2011, 133, 16402). The highlight of this work is the product divergence from [3+3] to [3+2] cycloaddition leading to 2,5-dihydroisoxazoles with clinical choice of substrate and catalyst.


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