ChemInform Abstract: Stereoselective Synthesis of Enantioenriched 2-Chloro-2-aroylaziridines by Cascade Reaction Between Aryl Nitriles, Silyldichloromethanes, and tert-Butanesulfinylimines

Silyldichloromethanes react in the presence of LDA to the corresponding alkyllithium intermediates, which undergo nucleophilic addition with aryl nitriles and subsequent [1,3]‐aza‐Brook rearrangement to dichlorocarbanions bearing α‐N‐silyl imines, which are then trapped by chiral sulfinylimines via...

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Veröffentlicht in:	ChemInform 2015-12, Vol.47 (2), p.no-no
Hauptverfasser:	Huang, Ze-Ao, Liu, Hui, Lu, Chong-Dao, Xu, Yan-Jun
Format:	Artikel
Sprache:	eng
Schlagworte:	annulation reactions aziridine derivatives cascade reactions cascade reactions, domino reactions, tandem reactions diastereoselective syntheses diastereoselective syntheses, enantioselective syntheses (incl. cis/trans‐isomerism) domino reactions enantioselective syntheses (incl. cis/trans-isomerism) multicomponent reactions ring closure reactions ring closure reactions, annulation reactions tandem reactions
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Beschreibung
Zusammenfassung:	Silyldichloromethanes react in the presence of LDA to the corresponding alkyllithium intermediates, which undergo nucleophilic addition with aryl nitriles and subsequent [1,3]‐aza‐Brook rearrangement to dichlorocarbanions bearing α‐N‐silyl imines, which are then trapped by chiral sulfinylimines via an aza‐Darzens‐type transformation.
ISSN:	0931-7597 1522-2667
DOI:	10.1002/chin.201602100