Catalytic Asymmetric Iodoesterification of Simple Alkenes
Catalytic Asymmetric Iodoesterification of Simple Alkenes
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DOI：
10.1002/anie.202003886
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发表时间：
2020-05-26
影响因子：
16.6
通讯作者：
Yamanaka, Masahiro
中科院分区：
文献类型：
--
作者：
Arai, Takayoshi;Horigane, Kodai;Yamanaka, Masahiro
用双核锌-3，3 '-（R，S，S）-双（氨基亚氨基）联萘氧化物（di-Zn）配合物催化简单烯烃的不对称碘化反应。对于使用对甲氧基苯甲酸的碘代化，N-碘代萘酰亚胺（NIN）-I-2系统是有效的，以高度对映选择性的方式产生碘代酯。手性碘代对甲氧基苯甲酸酯的合成效用也被证明。首次将金属离子键、氢键、卤素键和π-π堆积四重键协调在双锌催化剂的单反应球上，实现了简单烯烃的高对映选择性催化不对称碘代化反应。
Catalytic asymmetric iodoesterification of simple alkenes was achieved using a dinuclear zinc-3,3 '-(R,S,S)-bis(aminoimino)binaphthoxide (di-Zn) complex. For iodoesterification using p-methoxybenzoic acid, the N-iodonaphthalenimide (NIN)-I-2 system was effective for producing iodoesters in a highly enantioselective manner. The synthetic utility of chiral iodo-p-methoxybenzoates was also demonstrated. The quartet of metal ionic bond, hydrogen bond, halogen bond, and pi-pi stacking is harmonized on the single reaction sphere of di-Zn catalyst for enabling the highly enantioselective catalytic asymmetric iodoesterification of simple alkenes for the first time.