The Catalytic Regio- and Stereoselective Synthesis of 1,6-Diazabicyclo[4.3.0]nonane-2,7-diones - Normandie Université Access content directly
Journal Articles Journal of Organic Chemistry Year : 2021

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

Abstract

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 (KMC) 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 (ESI-IMS-MS) allowing to valid the proposed mechanism.
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Dates and versions

hal-03322396 , version 1 (19-08-2021)

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Cite

Arthur Lebrêne, Thomas Martzel, Laura Gouriou, Morgane Sanselme, Vincent Levacher, et al.. The Catalytic Regio- and Stereoselective Synthesis of 1,6-Diazabicyclo[4.3.0]nonane-2,7-diones. Journal of Organic Chemistry, 2021, 86 (13), pp.8600-8609. ⟨10.1021/acs.joc.1c00252⟩. ⟨hal-03322396⟩
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