Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 76, Issue 19, Pages 7849-7859Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo2012779
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Funding
- National Natural Science Foundation of China [20802074]
- National Basic Research Program of China (973 Program) [2010CB833300]
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An enantioselective 1,6-Michael addition reaction of arylthiols to a wide range of 3-methyl-4-nitro-5-alkenyl-isoxazoles catalyzed by readily available Takemoto's thiourea catalyst has been developed. This reaction provides a useful catalytic method for the synthesis of optically active chiral sulfur compounds bearing a 4-nitroisoxazol-5-yl moiety in high to excellent yields (up to 97%) and high enantioselectivities (up to 91% ee). Significantly, the potential utilities of the protocol had been further demonstrated by gram-scale reaction and the versatile conversions of some resulting products into other functionalized and useful compounds.
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