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引用本文的文献

1
Initial Examinations of the Diastereoselectivity and Chemoselectivity of Intramolecular Silyl Nitronate [3+2] Cycloadditions with Alkenyl/Alkynyl Nitroethers.分子内甲硅烷基硝酸酯与烯基/炔基硝基醚的[3+2]环加成反应的非对映选择性和化学选择性的初步研究
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本文引用的文献

1
Comparison of the accuracy of semiempirical and some DFT methods for predicting heats of formation.
J Mol Model. 2004 Feb;10(1):6-12. doi: 10.1007/s00894-003-0157-6. Epub 2003 Dec 4.
2
Intramolecular cycloaddition reactions of silyl nitronate tethered to vinylsilyl group: 2-nitroalkanols as precursors for amino polyols.与乙烯基硅烷基相连的硅基硝酸酯的分子内环加成反应：以2-硝基链烷醇作为氨基多元醇的前体。
Org Lett. 2003 Oct 16;5(21):3875-8. doi: 10.1021/ol035423v.
3
Sequential 1,3-dipolar cycloadditions in the synthesis of bis-isoxazolo substituted piperidinones.用于合成双异恶唑取代哌啶酮的连续1,3-偶极环加成反应。
J Org Chem. 2000 Jan 28;65(2):499-503. doi: 10.1021/jo991418m.

通过ISNC反应合成新型2H,5H-二氢呋喃-3-基酮

Synthesis of novel 2H,5H-Dihydrofuran-3-yl Ketones via ISNC reactions.

作者信息

Grandbois Matthew L, Betsch Kelsie J, Buchanan William D, Duffy-Matzner Jetty L

机构信息

Chemistry Dept., University of Minnesota, Minneapolis, Minnesota 55455-0431 USA.

出版信息

Tetrahedron Lett. 2009 Nov 25;50(47):6446-6449. doi: 10.1016/j.tetlet.2009.08.110.

DOI:10.1016/j.tetlet.2009.08.110
PMID:20161382
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC2782825/
Abstract

Unique 1-[2H,5H-dihydrofur-3-yl]ketones have been synthesized from propargylic nitroethers via intramolecular cycloadditions involving silyl nitronates. Various substituent groups were placed on the 2 and 5 positions of the dihydrofuran rings. We examined the scope of the long-range coupling in proton NMR of the oxo-dihydrofuran products. The identities of the diastereomers resulting from the Michael Addition/cycloaddition reactions were tentatively assigned for the first time. CAChe MNDO PM5 and CONFLEX programs were engaged to assist with the identification of these stereoisomers. The reaction times and conditions for these oxo-dihydrofurans were found to be different than that of the published dihydrofuranals, which led us to propose a different mechanism.

摘要

独特的1-[2H,5H-二氢呋喃-3-基]酮已通过涉及硅基硝酮的分子内环加成反应从炔丙基硝基醚合成。各种取代基被置于二氢呋喃环的2位和5位。我们研究了氧代二氢呋喃产物质子核磁共振中远程耦合的范围。首次初步确定了迈克尔加成/环加成反应产生的非对映异构体的身份。使用CAChe MNDO PM5和CONFLEX程序来辅助鉴定这些立体异构体。发现这些氧代二氢呋喃的反应时间和条件与已发表的二氢呋喃醛不同，这使我们提出了一种不同的反应机理。