Catalytic asymmetric 1,6-Michael addition of arylthiols to 3-methyl-4-nitro-5-alkenyl-isoxazoles with bifunctional catalysts.
Catalytic asymmetric 1,6-Michael addition of arylthiols to 3-methyl-4-nitro-5-alkenyl-isoxazoles with bifunctional catalysts.
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DOI：
10.1021/jo2012779
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发表时间：
2011-09
期刊：
影响因子：
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通讯作者：
Q. Pei;Hong Sun;Zhijun Wu;Xi‐Lin Du;Xiaomei Zhang;Weicheng Yuan
中科院分区：
文献类型：
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作者：
Q. Pei;Hong Sun;Zhijun Wu;Xi‐Lin Du;Xiaomei Zhang;Weicheng Yuan
本文报道了在Takemoto硫脲催化下芳基硫醇与3-甲基-4-硝基-5-烯基异恶唑的1，6-Michael加成反应。该反应提供了一种有用的催化方法，用于合成具有4-硝基异恶唑-5-基部分的光学活性的手性硫化合物，产率高达97%，对映选择性高达91%ee。值得注意的是，该方案的潜在效用已被进一步证明了克级反应和一些所得产物转化为其他功能化和有用的化合物的通用转换。
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.