N-杂环卡宾催化的串联氮杂苯并二氢吡喃/Michael 反应：N-Boc 亚胺反应活性的原位反转。
N-heterocyclic carbene-catalyzed tandem aza-benzoin/Michael reactions: on site reversal of the reactivity of N-Boc imines.
机构信息
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, PR China.
出版信息
Chem Commun (Camb). 2011 Jan 7;47(1):493-5. doi: 10.1039/c0cc01769h. Epub 2010 Oct 18.
PMID:20953492
Abstract
A tandem NHC-catalyzed aza-benzoin/Michael reaction has been developed as a method to efficiently produce dihydroindenones and pyrrolidinone-containing tricycles. The novel reaction pattern involves tert-butyl aryl(tosyl)methylcarbamates reacting as both electrophile and nucleophile on the same carbon.
摘要
已开发出一种串联 NHC 催化的氮杂苯偶姻/Michael 反应方法，可高效合成二氢茚酮和含吡咯烷酮的三环化合物。该新型反应模式涉及叔丁基芳基（对甲苯磺酰基）甲基氨基甲酸酯在同一碳原子上同时作为亲电试剂和亲核试剂反应。
相似文献
1
N-heterocyclic carbene-catalyzed tandem aza-benzoin/Michael reactions: on site reversal of the reactivity of N-Boc imines.
Chem Commun (Camb). 2011 Jan 7;47(1):493-5. doi: 10.1039/c0cc01769h. Epub 2010 Oct 18.
2
N-Heterocyclic carbene-catalyzed chemoselective cross-aza-benzoin reaction of enals with isatin-derived ketimines: access to chiral quaternary aminooxindoles.
Org Lett. 2014 Jun 20;16(12):3272-5. doi: 10.1021/ol501286e. Epub 2014 May 30.
3
Asymmetric intramolecular crossed-benzoin reactions by N-heterocyclic carbene catalysis.
Angew Chem Int Ed Engl. 2006 Feb 20;45(9):1463-7. doi: 10.1002/anie.200503885.
4
Enantioselective, cyclopentene-forming annulations via NHC-catalyzed benzoin-oxy-cope reactions.
J Am Chem Soc. 2007 Mar 28;129(12):3520-1. doi: 10.1021/ja0705543. Epub 2007 Mar 3.
5
Enantioselective synthesis of dihydropyridinones via NHC-catalyzed aza-Claisen reaction.
Org Lett. 2011 Oct 7;13(19):5378-81. doi: 10.1021/ol202272t. Epub 2011 Sep 9.
6
[4+2] cycloaddition of ketenes with N-benzoyldiazenes catalyzed by N-heterocyclic carbenes.
Angew Chem Int Ed Engl. 2009;48(1):192-5. doi: 10.1002/anie.200804487.
7
Enantioselective [4+2] cycloaddition of ketenes and 1-azadienes catalyzed by N-heterocyclic carbenes.
Chem Commun (Camb). 2011 Feb 28;47(8):2381-3. doi: 10.1039/c0cc04839a. Epub 2010 Dec 17.
8
N-heterocyclic carbene-catalyzed aza-Michael addition.
Org Biomol Chem. 2011 Oct 7;9(19):6715-20. doi: 10.1039/c1ob05429e. Epub 2011 Aug 11.
9
Thiazolium-derived N-heterocyclic carbene-catalyzed cross-coupling of aldehydes with unactivated imines.
Chem Commun (Camb). 2007 Feb 28(8):852-4. doi: 10.1039/b611646a. Epub 2006 Nov 23.
10
N-heterocyclic carbene-catalyzed [3+4] cycloaddition and kinetic resolution of azomethine imines.
J Am Chem Soc. 2014 Jan 29;136(4):1214-7. doi: 10.1021/ja411110f. Epub 2014 Jan 16.
引用本文的文献
1
Enantioselective annulation of enals with 2-naphthols by triazolium salts derived from l-phenylalanine.
Chem Sci. 2015 Jul 1;6(7):4273-4278. doi: 10.1039/c5sc00731c. Epub 2015 Apr 30.
Zotero 插件