Asymmetric aza-Diels-Alder reaction: Enantio- and diastereoselective reaction of imine mediated by Chiral Lewis acid
An efficient asymmetric aza-Diels-Alder reaction using chiral boron mediator is developed. The key to its success is the use of the chiral boron complex prepared in situ from (R)- or (S)- binaphthol and B(OPh)3. The enantiomeric reaction of prochiral imine affords products of up to 90% ee. The double asymmetric induction of chiral imine using α-benzylamine as a chiral auxiliary is achieved with almost complete diastereoselectivity for both aliphatic and aromatic aldimines. This method is applied to the efficient synthesis anabasine and coniine of piperidine alkaloides.
Asymmetric Aza-Diels-Alder Reaction Mediated by Chiral Boron Reagent
An asymmetric aza-Diels-Alder reaction of an imine mediated by an in situ generated chiral boron complex is described.The method is successful with several aldimines and affords products of up to 90percent ee.
Hattori, Kouji,Yamamoto, Hisashi
p. 3264 - 3265
(2007/10/02)
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