Process for the allylation of n-acylhydrazones

Details Process for the allylation of n-acylhydrazones Process for the allylation of n-acylhydrazones

2005-02-24

2010-02-09

O'Sullivan, Peter G (Department: 1621)

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

Organic compounds

Carboxylic acid esters

C562S524000, C562S575000

Reexamination Certificate

active

07659424

ABSTRACT:
[PROBLEMS] To provide a novel method for the allylation of N-acylhydrazones by which enantioselectively allylated N-acylhydrazines can be efficiently obtained.[MEANS FOR SOLVING PROBLEMS] A method for the production of enantioselectively allylated N-acylhydrazines represented by the general formula [3]:[wherein R0is an optionally substituted hydrocarbon group, an optionally substituted heterocyclic group, or —COOR1(wherein R1is a hydrocarbon group); R2is acyl; R3and R4are each hydrogen, or one of R3and R4is hydrogen and the other is a hydrocarbon group; and R5and R6are each independently hydrogen or a hydrocarbon group], characterized by reacting an N-acylhydrazone represented by the general formula [1]:[wherein R0and R2are as defined above] with an allylating agent such as allyltrichlorosilane or crotyltrichlorosilane in the presence of a chiral phosphine oxide.

REFERENCES:
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Ogawa et al., The Chemical Society of Japan Koen Yokoshu, 84(2):1270 (2004).
Ferraris et al., “Catalytic, Enantioselective Alkylations of N,O-Acetals”, J. Org. Chem., 64:2168-2169 (1999).
Hamada et al., “Catalytic Asymmetric Allylation of Hydrazono Esters in Aqueous Media by Using ZnF2-Chiral Diamine”, Angew. Chem. Int. Ed., 42:3927-3930 (2003).
Chikako Ogawa et al., “Stereospecific, Enantioselective Allylation of α-Hydrazono Esters by Using Allyltrichlorosilanes with BINAP Dioxides as Neutral-Coordinate Organocatalysts”,Angewandte Chemie, International Edition, 43(47), pp. 6491-6493 (2004).
Chikako Ogawa et al., “Phosphine Oxides as Efficient Neutral Coordinate-Organocatalysts for Stereoselective Allylation ofN-acylhydrazones”,Organic&Biomolecular Chemistry, 2(4), pp. 446-448 (2004).
Database WPI Week 200382,Derwent Publication Ltd., London, GB; XP-002464497; AN 2003-884288 (Sep. 25, 2003).

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