The Catalytic Regio- and Stereoselective Synthesis of 1,6-Diazabicyclo[4.3.0]nonane-2,7-diones | Zendy

Arthur Lebrêne | Zendy; Thomas Martzel | Zendy; Laura Gouriou | Zendy; Morgane Sanselme | Zendy; Vincent Levacher | Zendy; Sylvain Oudeyer | Zendy; Carlos Afonso | Zendy; Corinne LoutelierBourhis | Zendy; JeanFrançois Brière | Zendy

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The Catalytic Regio- and Stereoselective Synthesis of 1,6-Diazabicyclo[4.3.0]nonane-2,7-diones

Author(s) -

Arthur Lebrêne,

Thomas Martzel,

Laura Gouriou,

Morgane Sanselme,

Vincent Levacher,

Sylvain Oudeyer,

Carlos Afonso,

Corinne LoutelierBourhis,

JeanFrançois Brière

Publication year - 2021

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/acs.joc.1c00252

Subject(s) - chemistry , nonane , stereoselectivity , electrospray ionization , catalysis , michael reaction , knoevenagel condensation , mass spectrometry , conjugate , combinatorial chemistry , organic chemistry , stereochemistry , ion , chromatography , mathematical analysis , mathematics

A straightforward synthesis of original 1,6-diazabicyclo[4.3.0]nonane-2,7-diones was achieved through a DBU-organocatalyzed multicomponent Knoevenagel-aza-Michael-Cyclocondensation reaction which takes advantage of an unprecedented highly regio- and diastereoselective conjugate addition of pyridazinones to alkylidene Meldrum's acid intermediates. The key reactive intermediates of this complex process were analyzed by means of electrospray ionization mass spectrometry coupled to ion mobility spectrometry, allowing us to validate the proposed mechanism.

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