Catalytic asymmetric cyclopropanation of enones with dimethyloxosulfonium methylide promoted by a La-Li3-(Biphenyldiolate)3+NaI complex

Catalytic asymmetric cyclopropanation of enones with dimethyloxosulfonium methylide promoted by a La-Li3-(Biphenyldiolate)3+NaI complex
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DOI:
10.1021/ja076797c
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发表时间:
2007-11-07
影响因子:
15
通讯作者:
Shibasaki, Masakatsu
Shibasaki, Masakatsu
中科院分区:
化学1区
文献类型:
--
作者:
Kakei, Hiroyuki;Sone, Toshihiko;Shibasaki, Masakatsu

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描述了使用La− Li 3 −(biphenyldiolate)3+ NaI络合物催化的烯酮与二甲基氧锍亚甲基的不对称环丙烷化反应。本发明的方法在使用叶立德方面与先前报道的催化对映选择性方法互补,并且仅以良好的产率(96−73%)和高对映选择性(99− 84%ee)获得反式产物。使用联苯二醇1b-H2和碘化钠添加剂是必不可少的,以实现高的对映体选择性。
Catalytic asymmetric cyclopropanation of enones with dimethyloxosulfonium methylide using a La−Li3−(biphenyldiolate)3+ NaI complex is described. The present method is complementary to the previously reported catalytic enantioselective methods in terms of ylides used, and trans products were exclusively obtained in good yield (96−73%) and high enantioselectivity (99−84% ee). Use of biphenyldiol1b-H2and NaI additive was essential to achieve high enantioselectivity.