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A chiral oxazoline for catalytic enantioselective Nozaki-Hiyama-Kishi allylation and vinylation of aldehydes
Catalysis Communications ( IF 3.7 ) Pub Date : 2020-09-12 , DOI: 10.1016/j.catcom.2020.106166
Sharad V. Kumbhar , Chinpiao Chen

Asymmetric allylation and vinylation of aldehydes with allyl halides and vinyl halides have been achieved using the chromium(II)-oxazoline catalyst. The catalyst promotes the highly efficient enantioselective Nozaki–Hiyama-Kishi (NHK) allylation of aldehydes using allyl bromide, producing the corresponding homoallylic alcohols in good yields (up to 84%) and a high level of enantioselectivity (up to 98% ee). Meanwhile, the NHK vinylation of aldehydes produce desired allylic alcohols in satisfactory yields (up to 88%) and a high level of enantioselectivity (up to 97% ee). We developed a reliable and milder protocol for preparing chiral homoallylic and allylic alcohols.



中文翻译:

手性恶唑啉用于催化对映选择性的Nozaki-Hiyama-Kishi烯丙基化和醛的乙烯基化

使用铬(II)-恶唑啉催化剂已经实现了醛与烯丙基卤和乙烯基卤的不对称烯丙基化和乙烯基化。该催化剂使用烯丙基溴促进醛的高效对映选择性Nozaki-Hiyama-Kishi(NHK)烯丙基化,以高产率(最高84%)和高对映选择性(最高98%ee)产生相应的均烯丙基醇。同时,醛的NHK乙烯基化可以以令人满意的产率(高达88%)和高水平的对映选择性(高达97%ee)生产出所需的烯丙醇。我们开发了一种可靠且温和的方案来制备手性均烯丙基和烯丙基醇。

更新日期:2020-09-21
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