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Chiral Bisoxazoline Ligands in Catalytic Asymmetric Allylic Oxidation : Bisoxazoline Ligands in Asymmetric Reactions/Synthesis of Novel Bisoxazoline Ligands for Copper Catalyzed Asymmetric Allylic Oxi
Bok av Davoud Asgari
The Past three decades have witnessed a
major development in asymmetric catalysis in organic
synthesis. New and powerful catalysts have been designed
and developed which exhibit levels of enantioselectivity
previously considered beyond reach for non-enzymatic
processes. Nitrogen-based transition metal ligands such as
bisoxazoline ligands have emerged as an efficient class of
ligands in an increasing number of asymmetric
transformations including cyclopropanation, aziridination,
Diels-Alder reaction, reduction, aldol reaction, ene
reactions, allylic oxidation, and etc. This book reviews
the synthesis and applications of bisoxazoline-metal
complexes in a variety of asymmetric transformations and
then describes the design and synthesis of a novel class
of C2-symmetric biarylbisoxazoline ligands and their
application in copper catalyzed asymmetric allylic
oxidation of olefins. Potential applications for chiral
cycloalkenols derived from allylic oxidation are great. A
clear example is the conversion of (S)-cyclohexenyl
benzoate to the key aldehyde-methyl ester intermediate for
the synthesis of inflammation mediator leukotriene B4.