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本文引用的文献

1
Organocatalytic cascade reactions as a new tool in total synthesis.有机催化级联反应——全合成的新工具
Nat Chem. 2010 Mar;2(3):167-78. doi: 10.1038/nchem.539. Epub 2010 Feb 19.
2
Enantioselective and regioselective organocatalytic conjugate addition of malonates to nitroenynes.手性和区域选择性的有机催化丙二酸酯与硝基烯炔的共轭加成反应。
Chem Asian J. 2011 Jan 3;6(1):220-5. doi: 10.1002/asia.201000561.
3
Quinidine thiourea-catalyzed aldol reaction of unactivated ketones: highly enantioselective synthesis of 3-alkyl-3-hydroxyindolin-2-ones.奎尼丁硫脲催化的未活化酮的羟醛反应:3-烷基-3-羟基吲哚啉-2-酮的高对映选择性合成
Angew Chem Int Ed Engl. 2010 Dec 3;49(49):9460-4. doi: 10.1002/anie.201004161.
4
A unique approach to the concise synthesis of highly optically active spirooxazolines and the discovery of a more potent oxindole-type phytoalexin analogue.一种独特的方法,用于简洁合成高光学活性螺噁唑啉,并发现更有效的氧化吲哚型植物抗毒素类似物。
J Am Chem Soc. 2010 Nov 3;132(43):15328-33. doi: 10.1021/ja106349m.
5
Enantioselective synthesis of bicylco[3.2.1]octan-8-ones using a tandem Michael-Henry reaction.使用串联迈克尔 - 亨利反应对双环[3.2.1]辛烷 - 8 - 酮进行对映选择性合成。
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Catalytic enantioselective aldol additions of alpha-isothiocyanato imides to alpha-ketoesters.催化对映选择性α-异硫氰酸根合亚胺与α-酮酯的加成反应。
Chem Commun (Camb). 2010 Jul 7;46(25):4604-6. doi: 10.1039/c0cc00556h. Epub 2010 May 19.
7
The direct catalytic asymmetric aldol reaction.直接催化不对称醛醇缩合反应。
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8
Catalytic asymmetric domino Michael-Henry reaction: enantioselective access to bicycles with consecutive quaternary centers by using bifunctional catalysts.催化不对称多米诺迈克尔-亨利反应:使用双功能催化剂对具有连续季碳中心的双环化合物进行对映选择性合成。
Chemistry. 2010 Apr 12;16(14):4173-6. doi: 10.1002/chem.201000237.
9
Direct organocatalytic asymmetric aldol reaction of alpha-isothiocyanato imides to alpha-ketoesters under low ligand loading: a doubly stereocontrolled approach to cyclic thiocarbamates bearing chiral quaternary stereocenters.在低配体负载下,通过直接的有机催化不对称α-异硫氰酸根合亚胺与α-酮酯的Aldol 反应:一种双立体控制方法,用于合成具有手性季碳中心的环状硫代氨基甲酸酯。
Org Lett. 2010 Apr 2;12(7):1544-7. doi: 10.1021/ol1002829.
10
Organocatalytic enantioselective synthesis of both diastereomers of alpha-hydroxyphosphinates.有机催化对映选择性合成α-羟基膦酸盐的两种非对映异构体。
J Org Chem. 2010 Feb 19;75(4):1101-6. doi: 10.1021/jo9022099.

α-异硫氰酸酯亚胺与活性羰基化合物的有机催化对映选择性串联羟醛缩合-环化反应

Organocatalytic enantioselective tandem aldol-cyclization reaction of α-isothiocyanato imides and activated carbonyl compounds.

作者信息

Guang Jie, Zhao Cong-Gui

机构信息

Department of Chemistry, University of Texas at San Antonio, One UTSA Circle, San Antonio, Texas, 78249-0698, USA.

出版信息

Tetrahedron Asymmetry. 2011 Jun 15;22(11):1205-1211. doi: 10.1016/j.tetasy.2011.06.028.

DOI:10.1016/j.tetasy.2011.06.028
PMID:21921975
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC3171191/
Abstract

The organocatalytic enantioselective tandem aldol-cyclization reactions of α-isothiocyanato imides and activated carbonyl compounds, such as isatins, an α-ketolactone and a 1,2-dione, have been studied with cinchona alkaloid-derived thiourea-catalysts. This methodology provided an easy way to access enantiomerically enriched spirobicyclic thiocarbamates with high yields and good to excellent stereoselectivity, which have been demonstrated to be useful precursors for the synthesis of biologically active molecules.

摘要

使用金鸡纳生物碱衍生的硫脲催化剂,研究了α-异硫氰酸酯亚胺与活化羰基化合物(如异吲哚酮、α-酮内酯和1,2-二酮)的有机催化对映选择性串联羟醛缩合-环化反应。该方法提供了一种简便的途径,能够以高收率和良好至优异的立体选择性获得对映体富集的螺双环硫代氨基甲酸盐,已证明这些化合物是合成生物活性分子的有用前体。