Lewis Acid-catalysed Aza-Diels–Alder versus Mannich Reactions of N-Diethyl Phosphoryl Imino Dienophiles with Oxygenated Dienes and Application of a Chiral Lewis Acid

Di Bari, Lorenzo; Guillarme, S; Hermitage, S; Howard, Jak; Jay, Da; Pescitelli, Gennaro; Whiting, A; Yufitb, Ds

doi:10.1055/s-2004-817742

N-Phosphoryl imines react with oxygenated dienes in the presence of Lewis acids to provide either the formal aza-Diels-Alder adduct, or the acyclic Mannich-type addition product, depending upon the catalyst and work up used, which is in agreement with the hypothesis that these reactions are mediated by zwitterionic Lewis acid-complex intermediates, rather than a concerted cyclo-addition transition-state followed by hydrolytic ring opening. Stoichiometric asymmetric induction can be achieved using a zinc(II)binol complex, producing up 77% ee.

Autori interni:	DI BARI, LORENZO GUILLARME S HERMITAGE S HOWARD JAK JAY DA PESCITELLI, GENNARO WHITING A YUFITB DS mostra contributor esterni nascondi contributor esterni
Autori:	DI BARI L; GUILLARME S; HERMITAGE S; HOWARD JAK; JAY DA; PESCITELLI G; WHITING A; YUFITB DS
Titolo:	Lewis Acid-catalysed Aza-Diels–Alder versus Mannich Reactions of N-Diethyl Phosphoryl Imino Dienophiles with Oxygenated Dienes and Application of a Chiral Lewis Acid
Anno del prodotto:	2004
Digital Object Identifier (DOI):	10.1055/s-2004-817742
Appare nelle tipologie:	1.1 Articolo in rivista

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http://hdl.handle.net/11568/203375

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