α-(3,7-Dioxa-r-1-azabicyclo[3.3.0]oct-c-5-ylmethoxy)-diazines. Part 2: Functionalisation via directed ortho-metallation and cross-coupling reactions期刊界 All Journals 搜尽天下杂志传播学术成果专业期刊搜索期刊信息化学术搜索

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*α-(3,7-Dioxa-r-1-azabicyclo[3.3.0]oct-c-5-ylmethoxy)-diazines. Part 2: Functionalisation via directed ortho-metallation and cross-coupling reactions*

Authors:	Camelia Berghian Eric Condamine Alain Turck Carmen Maiereanu Mircea Darabantu

Institution:	^a Department of Organic Chemistry, ‘Babes-Bolyai’ University, 11 Aranyi Jànos Str., RO-400028 Cluj-Napoca, Romania ^b Institut de Recherche en Chimie Organique Fine (I.R.C.O.F.), Université de Rouen, BP 08, F-76131 Mont Saint-Aignan, France ^c Department of Inorganic Chemistry, ‘Babes-Bolyai’ University, 11 Aranyi Jànos Str., RO-400028 Cluj-Napoca, Romania

Abstract:	The functionalisation of the title compounds via regioselective Directed ortho-Metallation (DoM) and cross-coupling reactions is studied. The compatibility of the 3,7-DiOxa-r-1-AzaBicyclo3.3.0]Oct-c-5-ylmethoxy system (DOABO-CH₂O) to typical reaction conditions is established. Its role as Directed ortho-Metallation Group (DoMG) is examined, including competition with classical DoMGs, chlorine and methoxy. The chelating ability of some functionalised terms such as DOABO-CH₂O substituting chiral diarylmethanols and polyaza analogues of 2,6-terpyridine is discussed as intramolecular steric relationships determining configuration and aptitude to bind selectively transition metals, respectively.

Keywords:	Diazines Oxazolidines Metallation Cross-coupling NMR Chirality
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