β-Silyloxy allylboronate esters through an aldehyde borylation/homologation sequence

TETRAHEDRON LETTERS

卷:61

Article

Meyer, Gillian F.¹  Nistler, Maggie A.¹  Samoshin, Andrey, V^1,2  McManus, Brennan D.¹  Thane, Taylor A.¹  Ferber, Carl J.¹  O'Neil, Gregory W.²  Clark, Timothy B.¹ 

[1] Univ San Diego, Dept Chem & Biochem, 5998 Alcala Pk, San Diego, CA 92110 USA

[2] Western Washington Univ, Dept Chem, Bellingham, WA 98225 USA

关键词: alpha-Oxyboronate Esters;    Allyl Boronates;    Homologation;    Diboration;   

DOI  :  10.1016/j.tetlet.2020.152082

来源: Elsevier

【 摘 要 】

The areas of carbonyl borylation and the homologation of carbon-boron bonds have provided a number of fruitful methods in organic synthesis. Combining these approaches, the homologation of alpha-oxyboronate esters, provides pathways to access complex organoboronate esters stereoselectively. To this end, the homologation of alpha-silyloxyboronate esters with lithiated allyl chlorides to form beta-silyloxy allylboronate esters is reported. Direct oxidation of the homologation products provides beta-silyloxy allyl alcohols in good yield. The homologation provides a range of allylic alcohols, albeit with low diastereoselectivity. (C) 2020 Elsevier Ltd. All rights reserved.

【 授权许可】

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