Catalytic Asymmetric Halohydroxylation of α,β‐Unsaturated Ketones with Water as the Nucleophile,Advanced Synthesis & Catalysis

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Catalytic Asymmetric Halohydroxylation of α,β‐Unsaturated Ketones with Water as the Nucleophile
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2020-04-01 , DOI: 10.1002/adsc.202000080
Weiwei Li ₁ , Pengfei Zhou ₁ , Gonglin Li ₁ , Lili Lin ₁ , Xiaoming Feng ₁

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The catalytic asymmetric halohydroxylation of α,β‐unsaturated ketones with water as the nucleophile has been realized by applying a chiral N,N′‐dioxide/Fe(OTf)₂ complex as the catalyst. Bromo‐, chloro‐ and iodo‐hydroxylations were all suitable in this catalytic system. A variety of α‐halo‐β‐hydroxy ketones were obtained in often good yields with generally high dr and ee values. Besides, a Michael/α‐halogenation process was considered more possible and a possible transition state model was proposed to explain the origin of stereoselectivity.

中文翻译：

亲核试剂以水催化α，β-不饱和酮的不对称卤代羟基化反应

α的不对称催化halohydroxylation，用水β不饱和酮作为亲核试剂已经通过应用手性实现Ñ，N'二氧化物/铁（OTF）₂配合物作为催化剂。溴，氯和碘羟基化反应均适用于该催化体系。通常以高收率获得各种α-卤代-β-羟基酮，且其dr和ee值通常较高。此外，认为迈克尔/α-卤化过程更可能，并提出了可能的过渡态模型来解释立体选择性的起源。

更新日期：2020-04-01

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