Process for asymmetric intramolecular [3+2] cyclo-addition...

Details Process for asymmetric intramolecular [3+2] cyclo-addition... Process for asymmetric intramolecular [3+2] cyclo-addition...

2008-04-01

2008-04-01

Dentz, Bernard (Department: 5461)

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C546S017000, C548S357500, C548S360100, C548S360500

Reexamination Certificate

active

07351831

ABSTRACT:
An intramolecular [3+2] cycloaddition reaction of a hydrazone is carried out under a mild condition with a high stereoselectivity and yield by reacting a hydrazone derivative in the presence of an asymmetric catalyst system obtained by mixing a zirconium alkoxide represented by the following formula (I):in-line-formulae description="In-line Formulae" end="lead"?Zr(OR)4  (I)in-line-formulae description="In-line Formulae" end="tail"?(wherein R is a hydrocarbon group which may have a substituent) with a binaphthol derivative represented by the following formula (II):(wherein Y1and Y2are each identical or different and denote a hydrogen atom or a halogen atom, and at least one of Y1and Y2denotes a halogen atom).

REFERENCES:
Kobayashi, Shu et al., “Asymmetric Intramolecular [3+2] Cycloaddition Reactions of Acylhydrazones/Olefins Using a Chiral Zirconium Catalyst,”Journal of American Chemical Society(2002), 124(46), pp. 13678 to 13679.
Fouchet, B. et al., “(3+2) Intramolecular Cationic Cycloadditions and 1,3-Dipolar Cycloadditions of Phenylhydrazones”,Tetrahedron Letters(1981), 22(14), p. 1333-6.
Kobayashi, Shu et al., “Chiral Catalyst Optimization Using Both Solid-phase and Liquid-phase Methods in Asymmetric Aza Diels-Alder Reactions,”Organic Letters(2000), 2(9), pp. 1225 to 1227.
Sakane, Soichi et al., “Asymmetric Cyclization of Unsaturated Aldehydes Catalyzed by a Chiral,”Tetrahedron(1986), 42(8), p. 2203-9.

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