钯催化烯烃的不对称Aza-Wacker反应: 高效合成手性1,3-噁嗪烷-2-酮
收稿日期: 2022-08-16
修回日期: 2022-10-09
网络出版日期: 2022-10-12
基金资助
国家重点研发计划(2021YFA1500050); 国家自然科学基金(21971255); 国家自然科学基金(91956202); 国家自然科学基金(21790330); 国家自然科学基金(21821002); 中国科学院前沿科学重点研究计划(QYZDJSSW-SLH055); 中国科学院国际伙伴计划(121731KYSB20190016)
Asymmetric Palladium-Catalyzed Aza-Wacker Reaction of Alkenes: Efficient Synthesis of Chiral 1,3-Oxazinan-2-ones
Received date: 2022-08-16
Revised date: 2022-10-09
Online published: 2022-10-12
Supported by
National Key R&D Program of China(2021YFA1500050); National Natural Science Foundation of China(21971255); National Natural Science Foundation of China(91956202); National Natural Science Foundation of China(21790330); National Natural Science Foundation of China(21821002); Science and Technology Commission of Shanghai Municipality(19590750400); Science and Technology Commission of Shanghai Municipality(21520780100); Science and Technology Commission of Shanghai Municipality(17JC1401200); Key Research Program of Frontier Sciences of Chinese Academy of Sciences(QYZDJSSW-SLH055); International Partnership Program of Chinese Academy of Sciences(121731KYSB20190016)
报道了以氨基甲酸酯为氮亲核试剂的钯催化烯烃的分子内不对称aza-Wacker反应. 该反应利用C-6位丙基取代的吡啶噁唑啉为手性配体, 苯醌(BQ)为氧化剂, 以良好到优秀的产率、优秀的对映选择性实现了手性1,3-噁嗪烷-2-酮类化合物的高效合成, 机理研究表明反应通过烯烃的分子内不对称胺钯化启动, 继而发生烷基钯的β-氢消除得到目标产物.
关键词： 氮杂Wacker反应; 钯催化; 不对称胺钯化; 手性1,3-噁嗪烷-2-酮; 手性吡啶噁唑啉
杨新拓 , 陈品红 , 刘国生 . 钯催化烯烃的不对称Aza-Wacker反应: 高效合成手性1,3-噁嗪烷-2-酮[J]. 有机化学, 2022 , 42(10) : 3382 -3389 . DOI: 10.6023/cjoc202208021
A Pd-catalyzed asymmetric aza-Wacker-type reaction with N-Ts carbamate as the nucleophile has been developed, which employed a C-6 substituted pyridinyl-oxazoline as the chiral ligand and benzoquinone (BQ) as the oxidant. This reaction provides an efficient access to chiral 1,3-oxazinan-2-ones with good efficiency and excellent enantioselectivity. Mechanistic studies indicated that the reaction is initiated by an intramolecular asymmetric aminopalladation.
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