在低碱度“动力学”控制下(2S,3S)-α-(1-氧代异吲哚啉-3-基)甘氨酸的不对称合成

Asymmetric Synthesis of (2S,3S)-α-(1-Oxoisoindolin-3-yl)glycines under Low-Basicity "Kinetic" Control.

作者信息

Li Tingting, Zhou Shengbin, Wang Jiang, Aceña José Luis, Soloshonok Vadim A, Liu Hong

机构信息

Key Laboratory of Receptor Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences , 555 Zu Chong Zhi Road, Shanghai 201203, China.

School of Pharmacy, China Pharmaceutical University , Jiangsu, Nanjing 210009, China.

出版信息

J Org Chem. 2015 Nov 20;80(22):11275-80. doi: 10.1021/acs.joc.5b01730. Epub 2015 Nov 12.

DOI:10.1021/acs.joc.5b01730

Abstract

The previously illusive (2S,3S)-configured α-(1-oxoisoindolin-3-yl)glycines can be prepared under mild DBU-catalyzed, low-basicity conditions. The overall process includes a cascade of aldol addition, cyclization, rearrangement, and conjugate addition reactions, leading to the target products with moderate to good chemical yields and diastereoselectivity.

摘要

之前难以捉摸的(2S,3S)构型的α-(1-氧代异吲哚啉-3-基)甘氨酸可以在温和的DBU催化、低碱度条件下制备。整个过程包括一系列的羟醛加成、环化、重排和共轭加成反应，以中等至良好的化学产率和非对映选择性得到目标产物。

相似文献

1

Asymmetric Synthesis of (2S,3S)-α-(1-Oxoisoindolin-3-yl)glycines under Low-Basicity "Kinetic" Control.在低碱度“动力学”控制下(2S,3S)-α-(1-氧代异吲哚啉-3-基)甘氨酸的不对称合成

J Org Chem. 2015 Nov 20;80(22):11275-80. doi: 10.1021/acs.joc.5b01730. Epub 2015 Nov 12.

2

Direct synthesis of fused indoles by gold-catalyzed cascade cyclization of diynes.金催化二炔的级联环化直接合成稠合吲哚。

J Org Chem. 2011 Mar 4;76(5):1212-27. doi: 10.1021/jo102507c. Epub 2011 Jan 21.

3

Asymmetric [3 + 2] annulation of N-protected isatins with but-3-yn-2-one catalyzed by DIOP: facile creation of enantioenriched spiro[furan-2,3'-indoline]-2',4(5H)-dione.N-保护的色胺酮与丁-3-炔-2-酮的不对称 [3 + 2] 环加成反应，由 DIOP 催化：对映富集的螺[呋喃-2,3'-吲哚]-2',4(5H)-二酮的轻松构建。

Org Biomol Chem. 2012 Oct 28;10(40):8048-50. doi: 10.1039/c2ob25801c.

4

Palladium-catalyzed aryl amination-heck cyclization cascade: a one-flask approach to 3-substituted indoles.钯催化的芳基胺化-赫克环化串联反应：一种制备3-取代吲哚的单瓶法

Angew Chem Int Ed Engl. 2008;47(5):888-90. doi: 10.1002/anie.200703763.

5

Asymmetric chlorocyclization of indole-3-yl-benzamides for the construction of fused indolines.吲哚-3-基苯甲酰胺的不对称氯环化反应构建稠合吲哚啉。

Org Lett. 2014 May 2;16(9):2426-9. doi: 10.1021/ol5007532. Epub 2014 Apr 14.

6

Rhodium(I)-catalyzed cyclization reaction of o-alkynyl phenols and anilines. Domino approach to 2,3-disubstituted benzofurans and indoles.铑（I）催化的邻炔基苯酚与苯胺的环化反应。构建2,3-二取代苯并呋喃和吲哚的多米诺方法。

Org Lett. 2009 Mar 19;11(6):1329-31. doi: 10.1021/ol9001174.

7

N-heterocyclic carbene (NHC)-catalyzed highly diastereo- and enantioselective oxo-Diels-Alder reactions for synthesis of fused pyrano[2,3-b]indoles.N-杂环卡宾（NHC）催化的高非对映选择性和对映选择性的羰基 Diels-Alder 反应用于合成稠合的吡喃并[2,3-b]吲哚。

Org Lett. 2012 Jun 1;14(11):2894-7. doi: 10.1021/ol301175z. Epub 2012 May 18.

8

C–H bond functionalization via [1,5]-hydride shift/cyclization sequence: approach to spiroindolenines.通过[1,5]-氢迁移/环化序列实现的C-H键官能团化：合成螺吲哚啉的方法

J Org Chem. 2015 Jan 16;80(2):1155-62. doi: 10.1021/jo5026817.

9

Organocatalytic enantioselective Friedel-Crafts alkylation of 4,7-dihydroindoles with alpha,beta-unsaturated aldehydes: an easy access to 2-substituted indoles.4,7-二氢吲哚与α,β-不饱和醛的有机催化对映选择性傅克烷基化反应：一种简便合成2-取代吲哚的方法

Org Lett. 2009 May 21;11(10):2177-80. doi: 10.1021/ol900461v.

10

Enantioselective construction of pyrroloindolines via chiral phosphoric acid catalyzed cascade Michael addition-cyclization of tryptamines.手性磷酸催化的色胺的级联 Michael 加成-环化反应构建吡咯并吲哚啉的对映选择性。

Org Lett. 2012 Sep 7;14(17):4588-90. doi: 10.1021/ol302043s. Epub 2012 Aug 28.

引用本文的文献

1

Base-Promoted Synthesis of β-Substituted-Tryptophans via a Simple and Convenient Three-Component Condensation of Nickel(II) Glycinate.通过甘氨酸镍（II）简单便捷的三组分缩合反应实现碱促进的β-取代色氨酸的合成。

Molecules. 2017 Apr 27;22(5):695. doi: 10.3390/molecules22050695.

文献检索

告别复杂PubMed语法，用中文像聊天一样搜索，搜遍4000万医学文献。AI智能推荐，让科研检索更轻松。

立即免费搜索

文件翻译

保留排版，准确专业，支持PDF/Word/PPT等文件格式，支持 12+语言互译。

免费翻译文档

深度研究

AI帮你快速写综述，25分钟生成高质量综述，智能提取关键信息，辅助科研写作。

立即免费体验