1,2-Oxaborinan-3-enes 和 δ-Boryl 取代均烯丙基醇的立体和对映体选择性合成

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2024-11-19 DOI:10.1021/acs.orglett.4c0375510.1021/acs.orglett.4c03755

Zheye Zhang, and , Ming Chen*,

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引用次数: 0

摘要

报告了 1,2-氧硼烷-3-烯和δ-硼代均烯丙基醇的立体和对映选择性合成。我们开发了一种实用的方法来合成α-苄基取代的烯丙基硼酸酯。利用这种试剂生成了 α,α-二取代的烯丙基硼酸酯，而这种试剂无法通过 Pd 催化的烯烃异构化方法获得。用这些试剂进行手性勃氏酸催化醛加成，可以得到立体选择性和对映体选择性极佳的 1,2-氧硼烷-3-烯。路易斯酸催化的醛加成反应也很有效，可以得到立体选择性很高的δ-硼代均烯丙基醇。该反应的对映选择性变体是通过手性勃氏酸催化醛加成和钯催化烯异构化方法实现的。

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Stereo- and Enantioselective Syntheses of 1,2-Oxaborinan-3-enes and δ-Boryl-Substituted Homoallylic Alcohols

Stereo- and enantioselective syntheses of 1,2-oxaborinan-3-enes and δ-boryl-substituted homoallylic alcohols are reported. We developed a practical approach to synthesize α-boryl-substituted allylboronate. This reagent was utilized to generate α,α-disubstituted allylboronates, and such reagents cannot be accessed via the Pd-catalyzed alkene isomerization approach. Chiral Brønsted-acid-catalyzed aldehyde addition with these reagents gave 1,2-oxaborinan-3-enes with excellent stereo- and enantioselectivities. Lewis-acid-catalyzed aldehyde addition also worked well, affording δ-boryl-substituted homoallylic alcohols with high stereoselectivities. The enantioselective variant of the reaction was achieved via a chiral Brønsted-acid-catalyzed aldehyde addition and Pd-catalyzed alkene isomerization approach.

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.