Stereoselective cascade reactions for construction of polyfunctionalised octahydroquinolines via [2C+2C+1C,1N] cyclisation

A conceptually unifying approach for a highly enantio- and diastereoselective synthesis of polyfunctionalised octrahydroquinolines incorporating three contiguous chiral centres is reported. The synthesis involves diphenylprolinol silyl ether-catalysed Michael addition of 1,3-cyclohexanedione to nitr...

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Veröffentlicht in:	Tetrahedron letters 2011-03, Vol.52 (12), p.1354-1358
Hauptverfasser:	Rai, Ankita, Singh, Atul K., Singh, Pankaj, Yadav, Lal Dhar S.
Format:	Artikel
Sprache:	eng
Schlagworte:	[2+2+2] Annulation Carbonates Cascade chemical reactions Cascade reaction Cascades Chemistry Construction Dehydration Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives Nitroalkenes Organic chemistry Organocatalysis Potassium Preparations and properties Quinolines Stereoselective synthesis Synthesis (chemistry) Tetrahedrons
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Beschreibung
Zusammenfassung:	A conceptually unifying approach for a highly enantio- and diastereoselective synthesis of polyfunctionalised octrahydroquinolines incorporating three contiguous chiral centres is reported. The synthesis involves diphenylprolinol silyl ether-catalysed Michael addition of 1,3-cyclohexanedione to nitroalkenes followed by potassium carbonate-promoted aza-Henry reaction with N-tosyl aldimines, intramolecular hemiaminalisation and dehydration reaction cascade in a one-pot operation.
ISSN:	0040-4039 1873-3581
DOI:	10.1016/j.tetlet.2011.01.079