NMR studies of the gold(I)-catalyzed asymmetric aldol reaction of isocyanoacetate
โ Scribed by Masaya Sawamura; Yoshihiko Ito; Tamio Hayashi
- Book ID
- 104226698
- Publisher
- Elsevier Science
- Year
- 1990
- Tongue
- French
- Weight
- 237 KB
- Volume
- 31
- Category
- Article
- ISSN
- 0040-4039
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โฆ Synopsis
A ferrocenylphosphine-silver-isocyanoacetate complex was investigated as a model compound for catalytic species in gold-catalyzed aldol reaction. 'H{lH} NOE studies of the silver complex indicated that terminal amino group of pendant side chain of the ferrocenylphosphine ligand is located close to active hydrogens of isocyanoacetate coordinated.
๐ SIMILAR VOLUMES
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
Asymmetric aldol reaction of methyl a-lsoryanoacetate with (&2-hexadecenal In the presence of 1 mol% of a choral (amlnoalkyl)ferrocenylphosphlne-gold(I) romplex gave optirally active trans-4-(methoxycarbonyl)-5-((E)-l-pentade~enyl)-2-oxazollne (93% ee) which was readily converted into Q-threo-and er