Ni-DBFOX/Ph催化N-α,β-不饱和酰基吡唑与C,N-二芳基硝酮的不对称1,3-偶极环加成反应
收稿日期: 2016-08-23
修回日期: 2016-09-13
网络出版日期: 2016-09-19
基金资助
国家自然科学基金（No. 21506043）和黑龙江省绿色化工技术创新团队（No. 2014TD007）资助项目.
Asymmetric 1,3-Dipolar Cycloaddition Reaction of C,N-Diarylnitrone with N-α,β-Unsaturated Acylpyrazoles Catalyzed by Ni-DBFOX/Ph
Received date: 2016-08-23
Revised date: 2016-09-13
Online published: 2016-09-19
Supported by
Project supported by the National Natural Science Foundation of China(No. 21506043) and the Innovative Research Team Foundation of Green Chemical Technology in the University of Heilongjiang Province(No. 2014TD007).
报道了（R，R）-4，6-二苯并呋喃二基-2，2'-双-4-苯基噁唑啉镍（Ni-DBFOX）型手性催化剂催化N-α，β-不饱和酰基吡唑与C，N-二芳基硝酮的不对称1，3-偶极环加成反应.研究结果表明，在10%催化剂存在下，反应的区域选择性为95：5，endo/exo选择性为99：1，ee值达到90%以上.对烯烃、硝酮结构、金属盐种类以及催化剂用量对反应的立体选择性影响进行了讨论.
关键词： 不对称催化; 1,3-偶极环加成反应; DBFOX/Ph; C,N-二芳基硝酮; N-(α,β-不饱和)酰基吡唑; 对映体选择性
刘迅绅 , 李美美 , 由君 , 刘波 . Ni-DBFOX/Ph催化N-α,β-不饱和酰基吡唑与C,N-二芳基硝酮的不对称1,3-偶极环加成反应[J]. 有机化学, 2017 , 37(1) : 86 -91 . DOI: 10.6023/cjoc201608019
Using(R,R)-4,6-dibenzofurandiyl-2,2'-bis(4-phenyloxazoline)-Ni(Ni-DBFOX) as the catalyst,asymmetric catalytic 3-dipolar cycloaddition reactions between N-α,β-unsaturated acylpyrazoles and C,N-diarylnitrone have been developed with 95% regioselectivity and an endo/exo ratio of 99:1 with >90% ee of the endo-diastereomer.Influence of olefins,nitrone structure,metal type and amount of catalyst on the reaction stereoselectivity was also carefully discussed.
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