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Asymmetric aldol reaction of α-ketoesters with isocyanoacetate and isocyanoacetamide catalyzed by a chiral ferrocenylphosphine-gold(I) complex

✍ Scribed by Yoshihiko Ito; Masaya Sawamura; Hitoshi Hamashima; Takashi Emura; Tamio Hayashi

Publisher
Elsevier Science
Year
1989
Tongue
French
Weight
267 KB
Volume
30
Category
Article
ISSN
0040-4039

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✦ Synopsis

summsry: Asymmetric aldol reaction of a-ketoesters (RCOCCCMe: R = Me, i-Bu, ph) with methyl isocyanoacetate or N,N-dimethyl-a-isocyanoacetamide in the presence of 1 molX of a chiral (arinoalkyl)ferrocenylphosphine-gold(I) catalyst proceeded with high enantioselectivity to give corresponding oxazolines of up to 90% ee, which were converted into optically active B-alkyl-b-hydroxyaspartic acid derivatives.

We have found that the gold(I) complex coordinated with an optically active ferrocenylphosphine ligand bearing Z-(dialkylamino)ethylanino side chain is an effective

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