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串联同系化-酰化化学:单同系化和双同系化

Tandem Homologation-Acylation Chemistry: Single and Double Homologation.

作者信息

Henderson Carley S, Mazzone Jennifer R, Moore Amanda M, Zercher Charles K

机构信息

Department of Chemistry, University of New Hampshire, Durham, NH 03824.

出版信息

Tetrahedron. 2021 Jul 2;91. doi: 10.1016/j.tet.2021.132223. Epub 2021 May 19.

Abstract

Treatment of β-dicarbonyls with the Furakawa-variant of the Simmons-Smith reagent results in homologation and production of an intermediate zinc enolate. Treatment of the enolate with various acylating agents generate products with both γ-dicarbonyl functionality and β-dicarbonyl functionality. In situ exposure of the acylated product to additional zinc carbenoid effects a second regiospecific homologation reaction.

摘要

用Simmons-Smith试剂的古川变体处理β-二羰基化合物会导致同系化并生成中间体锌烯醇盐。用各种酰化剂处理烯醇盐会生成具有γ-二羰基官能团和β-二羰基官能团的产物。酰化产物原位暴露于额外的锌卡宾会引发第二次区域特异性同系化反应。

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Reaction pathways of the Simmons-Smith reaction.西蒙斯-史密斯反应的反应途径。
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本文引用的文献

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Tandem chain extension-aldol reaction: syn selectivity with a zinc enolate.
Org Lett. 2001 Dec 27;3(26):4169-71. doi: 10.1021/ol016788n.
10
Zinc-mediated chain extension of beta-keto phosphonates.
J Org Chem. 2000 Sep 8;65(18):5615-22. doi: 10.1021/jo000343f.

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