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Asymmetric synthesis of β-hydroxy-α-alkylamino acids by asymmetric aldol reaction of α-isocyanocarboxylates catalyzed by chiral ferrocenylphosphine-gold(I) complexes

✍ Scribed by Yoshihiko Ito; Masaya Sawamura; Eiji Shirakawa; Keiichi Hayashizaki; Tamio Hayashi

Publisher
Elsevier Science
Year
1988
Tongue
French
Weight
768 KB
Volume
44
Category
Article
ISSN
0040-4020

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✦ Synopsis

Aldol reaction of methyl o-isocyanocarboxylates (CNCH(R)aXmc: R -H. Me, Et, i_Pr)th kntaldehyde or acetaldchyde in the presence of 0.5-1.0 molX of a chiral ~aainoalkyl)ferrocenylphosphine-Sold(I) complex Rave optically active G-methoxycarbonyl-6,5-dialkyl-2-oxszolines with high ensntioaelcctivity in a quantitatlvc yield. The oxarolines were converted into optically active B-hydroxy-a-alkylamino acid methyl esters. H Me ?I Au(l)/1 f?; COOMCI . .

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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 oxazolin