Asymmetric Synthesis of Pipecolic Acid Derivatives Using the Aza-Diels-Alder Reaction
Imines of the type R-N=CHCO2Et can be coerced into undergoing a (4+2) cycloaddition with substituted dienes if the reaction is carried out in DMF in the presence of both water and acid; these reactions show extremely high regio- and diastereoselectivity.U
Bailey, Patrick D.,Brown, George R.,Korber, Fritjof,Reed, Amanda,Wilson, Robert D.
p. 1263 - 1282
(2007/10/02)
Enantio- and Diastereo-selective Synthesis of Pipecolic Acid Derivatives using the Aza-Diels-Alder Reaction of Imines with Dienes
Optically active pipecolic acid derivatives can be prepared by the aza-Diels-Alder reaction of simple dienes with the imine derived from ethyl glyoxylate and chiral 1-phenylethylamine; the cycloadditions are regiospecific, highly diastereoselective within the heterocyclic ring (>92percent exo with cyclic dienes, and 100percent endo with acyclic dienes), and lead to high asymmetric induction in most cases (average d.e. = 72percent).
Bailey, Patrick D.,Wilson, Robert D.,Brown, George R.
p. 1337 - 1340
(2007/10/02)
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