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DOI: 10.1055/s-0033-1340433
Rh2(R-TPCP)4-Catalyzed Enantioselective Syntheses of 2,5-Dihydroisoxazoles
Publication History
Publication Date:
13 December 2013 (online)
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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