4.6 Article

A chiral oxazoline for catalytic enantioselective Nozaki-Hiyama-Kishi allylation and vinylation of aldehydes

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CATALYSIS COMMUNICATIONS
卷 148, 期 -, 页码 -

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ELSEVIER
DOI: 10.1016/j.catcom.2020.106166

关键词

Asymmetric allylation; Asymmetric vinylation; Oxazoline ligand; Nozaki-Hiyama-Kishi; Enantioselectivity

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  1. Ministry of Science and Technology, Taiwan [MOST: 1082113-M-277-001]

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Asymmetric allylation and vinylation of aldehydes using chromium(II)-oxazoline catalyst have been achieved, leading to high yields and enantioselectivity of homoallylic alcohols and allylic alcohols. The developed protocol offers a reliable and milder method for preparing chiral homoallylic and allylic alcohols.
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.

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