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本文引用的文献

1
Stereoselectivity in Oxyallyl-Furan 4+3 Cycloadditions: Control of Intermediate Conformations and Dispersive Stabilisation with Evans' Oxazolidinones.氧代烯丙基-呋喃4+3环加成反应中的立体选择性：利用伊文斯恶唑烷酮控制中间体构象和分散稳定作用
Chem Sci. 2010 Sep 1;1(3):387-392. doi: 10.1039/C0SC00280A.
2
Ligand-controlled regioselectivity in palladium-catalyzed cross coupling reactions.钯催化交叉偶联反应中的配体控制区域选择性。
J Am Chem Soc. 2010 Mar 3;132(8):2496-7. doi: 10.1021/ja9077528.
3
Origin of stereoselectivity in the (4 + 3) cycloadditions of chiral alkoxy siloxyallyl cations with furan.手性烷氧基硅氧基烯丙基阳离子与呋喃的[4 + 3]环加成反应中立体选择性的起源。
Org Lett. 2010 Feb 5;12(3):444-7. doi: 10.1021/ol902591k.
4
The lowest singlet and triplet States of the oxyallyl diradical.氧烯丙基双自由基的最低单重态和三重态。
Angew Chem Int Ed Engl. 2009;48(45):8509-11. doi: 10.1002/anie.200904417.
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Inter- and intramolecular [4 + 3] cycloadditions using epoxy enol silanes as functionalized oxyallyl cation precursors.使用环氧烯醇硅烷作为官能化氧烯丙基阳离子前体的分子间和分子内[4 + 3]环加成反应。
J Am Chem Soc. 2009 Apr 8;131(13):4556-7. doi: 10.1021/ja807566t.
6
Transition state distortion energies correlate with activation energies of 1,4-dihydrogenations and Diels-Alder cycloadditions of aromatic molecules.过渡态畸变能与芳香族分子的1,4-双氢化反应和狄尔斯-阿尔德环加成反应的活化能相关。
J Am Chem Soc. 2009 Mar 25;131(11):4084-9. doi: 10.1021/ja809142x.
7
Theory of 1,3-dipolar cycloadditions: distortion/interaction and frontier molecular orbital models.1,3 -偶极环加成反应理论：扭曲/相互作用和前沿分子轨道模型
J Am Chem Soc. 2008 Aug 6;130(31):10187-98. doi: 10.1021/ja800009z. Epub 2008 Jul 10.
8
Highly stereoselective [4 + 3] cycloadditions of nitrogen-stabilized oxyallyl cations with pyrroles: an approach to parvineostemonine.氮稳定的氧烯丙基阳离子与吡咯的高度立体选择性[4 + 3]环加成反应：一种合成帕维新蒙宁的方法。
Org Lett. 2007 Mar 29;9(7):1275-8. doi: 10.1021/ol070103n. Epub 2007 Mar 3.
9
Chiral Lewis acid-catalyzed highly enantioselective [4 + 3] cycloaddition reactions of nitrogen-stabilized oxyallyl cations derived from allenamides.手性路易斯酸催化由烯丙酰胺衍生的氮稳定氧化烯丙基阳离子的高度对映选择性[4 + 3]环加成反应。
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10
Understanding the nature of the molecular mechanisms associated with the competitive Lewis acid catalyzed [4+2] and [4+3] cycloadditions between arylidenoxazolone systems and cyclopentadiene: a DFT analysis.理解与芳亚甲基恶唑酮体系和环戊二烯之间竞争性路易斯酸催化的[4+2]和[4+3]环加成反应相关的分子机制的本质：一项密度泛函理论分析。
Chemistry. 2004 Oct 4;10(19):4742-9. doi: 10.1002/chem.200400277.

呋喃与唑烷酮取代的氧杂丙烯之间的（4 + 3）环加成的区域选择性。

Regioselectivities of (4 + 3) cycloadditions between furans and oxazolidinone-substituted oxyallyls.

机构信息

Division of Pharmaceutical Sciences and Department of Chemistry, University of Wisconsin, Madison, Wisconsin 53705, USA.

出版信息

Org Lett. 2010 Dec 3;12(23):5506-9. doi: 10.1021/ol1023745. Epub 2010 Nov 4.

DOI:10.1021/ol1023745
PMID:21049917
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC2993829/
Abstract

The (4 + 3) cycloadditions of oxazolidinone-substituted oxyallyls and unsymmetrically substituted furans lead to syn regioselectivity when the furan has a 2-Me or 2-COOR substituent, while anti regioselectivity is obtained with a 3-Me or 3-COOR group. DFT calculations are performed to explain the selectivities. The reactivities and regioselectivities are consistent with the ambiphilic reactivity of amino-oxyallyls with furans.

摘要

（4 + 3）环加成反应的恶唑烷酮取代的氧杂丙烯和不对称取代的呋喃导致顺式区域选择性，当呋喃具有 2-Me 或 2-COOR 取代基时，而反式区域选择性则得到 3-Me 或 3-COOR 基团。进行了 DFT 计算以解释选择性。反应性和区域选择性与氨基-氧杂丙烯与呋喃的两性反应性一致。