Asymmetric Construction of Quaternary Stereocenters: Synthesis of Enantiopure Amino Acid‐Based Tricyclic α,β‐Enones through an  ipso ‐Friedel–Crafts/Michael Addition Cascade | Zendy

RodríguezSolla Humberto | Zendy; Concellón Carmen | Zendy; Tuya Paula | Zendy; GarcíaGranda Santiago | Zendy; Díaz M. Rosario | Zendy

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Asymmetric Construction of Quaternary Stereocenters: Synthesis of Enantiopure Amino Acid‐Based Tricyclic α,β‐Enones through an ipso ‐Friedel–Crafts/Michael Addition Cascade

Author(s) -

RodríguezSolla Humberto,

Concellón Carmen,

Tuya Paula,

GarcíaGranda Santiago,

Díaz M. Rosario

Publication year - 2012

Publication title -

advanced synthesis and catalysis

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.541

H-Index - 155

eISSN - 1615-4169

pISSN - 1615-4150

DOI - 10.1002/adsc.201100497

Subject(s) - enantiopure drug , chemistry , friedel–crafts reaction , stereocenter , michael reaction , phosphoric acid , tricyclic , cascade , boron trifluoride , stereochemistry , cascade reaction , organic chemistry , enantioselective synthesis , catalysis , chromatography

An efficient reaction of the (2 R ,1′ S )‐ or (2 S ,1′ S )‐ N,N ‐bis( p ‐methoxybenzyl)‐2‐(1‐aminoalkyl)epoxides, derived from α‐amino acids, with boron trifluoride‐phosphoric acid complex is described. This process affords highly elaborated enantiopure tricyclic α,β‐enones in high yields, through an ipso ‐Friedel–Crafts/Michael addition cascade.

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