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本文引用的文献

1
From discovery to application: 50 years of the vinylcyclopropane-cyclopentene rearrangement and its impact on the synthesis of natural products.从发现到应用:乙烯基环丙烷 - 环戊烯重排反应的50年及其对天然产物合成的影响
Angew Chem Int Ed Engl. 2010 Jul 5;49(29):4864-76. doi: 10.1002/anie.200906001.
2
Practical and highly selective sulfur ylide mediated asymmetric epoxidations and aziridinations using an inexpensive, readily available chiral sulfide. Applications to the synthesis of quinine and quinidine.实用且高对映选择性的硫叶立德介导不对称环氧化和氮杂环丙烷化反应,使用廉价、易得的手性硫化物。在奎宁和奎尼丁合成中的应用。
J Am Chem Soc. 2010 Feb 17;132(6):1828-30. doi: 10.1021/ja9100276.
3
Creative approaches towards the synthesis of 2,5-dihydro- furans, thiophenes, and pyrroles. One method does not fit all!合成2,5 - 二氢呋喃、噻吩和吡咯的创新方法。一种方法并不适用于所有情况!
Org Biomol Chem. 2009 May 7;7(9):1761-70. doi: 10.1039/b900236g. Epub 2009 Mar 11.
4
Rearrangement of N-aryl-2-vinylaziridines to benzoazepines and dihydropyrroles: a synthetic and theoretical study.N-芳基-2-乙烯基氮杂环丙烷重排为苯并氮杂䓬和二氢吡咯:一项合成与理论研究。
Chemistry. 2009;15(5):1241-51. doi: 10.1002/chem.200801148.
5
Lewis acid catalyzed [1,3]-sigmatropic rearrangement of vinyl aziridines.路易斯酸催化的乙烯基氮杂环丙烷的[1,3]-σ迁移重排反应。
Org Lett. 2008 Nov 6;10(21):5023-6. doi: 10.1021/ol802123e. Epub 2008 Oct 9.
6
Cooperative, highly enantioselective phosphinothiourea catalysis of imine-allene [3 + 2] cycloadditions.膦酰基硫脲对亚胺-丙二烯[3 + 2]环加成反应的协同、高对映选择性催化作用。
J Am Chem Soc. 2008 Apr 30;130(17):5660-1. doi: 10.1021/ja801344w. Epub 2008 Apr 8.
7
Adventures in sulfur-nitrogen chemistry.硫氮化学的探索之旅。
J Org Chem. 2006 Nov 24;71(24):8993-9003. doi: 10.1021/jo061027p.
8
Functionalized chiral vinyl aminosulfoxonium salts: asymmetric synthesis and application to the synthesis of enantiopure unsaturated prolines, beta,gamma-dehydro amino acids, and cyclopentanoid keto aminosulfoxonium ylides.功能化手性乙烯基氨磺鎓盐:不对称合成及其在对映体纯不饱和脯氨酸、β,γ-脱氢氨基酸和环戊烷类酮氨磺鎓叶立德合成中的应用
J Am Chem Soc. 2006 Jun 7;128(22):7360-73. doi: 10.1021/ja061152i.
9
Asymmetric synthesis of trans-2,5-disubstituted pyrrolidines from enantiopure homoallylic amines. Synthesis of pyrrolidine (-)-197B.由对映体纯的高烯丙基胺不对称合成反式-2,5-二取代吡咯烷。吡咯烷(-)-197B的合成。
J Org Chem. 2006 Mar 31;71(7):2779-86. doi: 10.1021/jo052566h.
10
Enantioselective, palladium-catalyzed alpha-arylation of N-Boc-pyrrolidine.钯催化的N-叔丁氧羰基吡咯烷的对映选择性α-芳基化反应
J Am Chem Soc. 2006 Mar 22;128(11):3538-9. doi: 10.1021/ja0605265.

手性乙烯基氮丙啶的立体特异性环扩张。

Stereospecific ring expansion of chiral vinyl aziridines.

机构信息

Department of Chemistry and Chemical Biology, Cornell University , Ithaca, New York 14853, USA.

出版信息

Org Lett. 2011 Mar 4;13(5):1110-3. doi: 10.1021/ol200263g. Epub 2011 Feb 10.

DOI:10.1021/ol200263g
PMID:21309528
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC3072884/
Abstract

In this report, it is demonstrated that chiral vinyl aziridines can be stereospecifically ring expanded. This synthetic approach allows controlled access to chiral 2,5-cis- or 2,5-trans-3-pyrroline products from starting materials with the appropriate aziridine geometry. Twenty three ring expansion examples, most of which feature a stereospecific cyclization, are presented.

摘要

在本报告中,证明了手性乙烯基氮丙啶可以进行立体特异性环扩张。这种合成方法允许从具有适当氮丙啶几何形状的起始原料中控制地获得手性 2,5-顺式或 2,5-反式-3-吡咯啉产物。提出了二十三个环扩张实例,其中大多数具有立体特异性的环化。