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本文引用的文献

1
Towards the Total Synthesis of Marineosin A: Construction of the Macrocyclic Pyrrole and an Advanced, Functionalized Spiroaminal Model.迈向海生素A的全合成：大环吡咯的构建及一个高级功能化螺胺模型
European J Org Chem. 2013 Jul 1;2013(20). doi: 10.1002/ejoc.201300643.
2
Tandem chain extension-Mannich reaction: an approach to β-proline derivatives.串联链延伸-曼尼希反应：一种合成β-脯氨酸衍生物的方法。
Tetrahedron. 2012 Sep 23;68(38):7799-7805. doi: 10.1016/j.tet.2012.07.039. Epub 2012 Jul 17.
3
Syntheses of papyracillic acids: application of the tandem chain extension-acylation reaction.帕比培南酸的合成：串联链延伸-酰化反应的应用。
J Org Chem. 2012 Oct 19;77(20):9171-8. doi: 10.1021/jo3017617. Epub 2012 Oct 5.
4
Carbamoylation of aryl halides by molybdenum or tungsten carbonyl amine complexes.钼或钨羰基氨配合物对芳基卤化物的氨甲酰化作用。
J Org Chem. 2010 May 7;75(9):3017-20. doi: 10.1021/jo1002592.
5
A new facile approach to the synthesis of 3-methylthio-substituted furans, pyrroles, thiophenes, and related derivatives.一种合成3-甲硫基取代的呋喃、吡咯、噻吩及相关衍生物的简便新方法。
J Org Chem. 2008 May 2;73(9):3377-83. doi: 10.1021/jo702585s. Epub 2008 Mar 20.
6
Solution phase synthesis of a library of tetrasubstituted pyrrole amides.四取代吡咯酰胺文库的溶液相合成。
J Comb Chem. 2006 Jul-Aug;8(4):491-9. doi: 10.1021/cc060008q.
7
Zinc carbenoid-mediated chain extension: preparation of alpha,beta-unsaturated-gamma-keto esters and amides.锌卡宾介导的链增长反应：α,β-不饱和-γ-酮酯和酰胺的制备
J Org Chem. 2003 May 30;68(11):4535-8. doi: 10.1021/jo026299g.
8
Tandem chain extension-aldol reaction: syn selectivity with a zinc enolate.
Org Lett. 2001 Dec 27;3(26):4169-71. doi: 10.1021/ol016788n.
9
Tandem chain extension-homoenolate formation: the formation of alpha-methylated-gamma-keto esters.
Org Lett. 2001 Sep 20;3(19):3037-40. doi: 10.1021/ol016485t.
10
Zinc-mediated chain extension of beta-keto phosphonates.
J Org Chem. 2000 Sep 8;65(18):5615-22. doi: 10.1021/jo000343f.

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.

DOI:10.1016/j.tet.2021.132223
PMID:34421135
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC8372754/
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。