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Asymmetric synthesis of 3-substituted dihydroisocarbostyril derivatives

✍ Scribed by Toshio Wakabayashi; Kenzo Watanabe

Book ID
104235875
Publisher
Elsevier Science
Year
1977
Tongue
French
Weight
181 KB
Volume
18
Category
Article
ISSN
0040-4039

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✦ Synopsis

Despite well-developed methodology for the carbon-carbon bond formation at C-l position in isoquinoline skeleton (e.g., Reissert reaction'), there is no comparable procedure for the introduction of an alkyl group at C-3 position in dihydroisocarbostyril derivatives. We have recently developed a novel asymmetric syntheses of Z-oxo-S-pyrrolidineacetic acid and 2-oxo-6-piperidineacetic acid by Wittig-Horner reaction of S-hydroxy pyrrolidone and 6-hydroxy piperidone derivatives respectively. 2,3 In this report we describe a facile method for the introduction of an alkyl group at C-3 position in heterocyclic nuclei of isocarbostyril derivatives, which is both general and asymmetric.

Reaction of homophthalic acid with (S)-(-)-a-phenethylamine at 2OO'C for

πŸ“œ SIMILAR VOLUMES

Asymmetric carbonβ€”carbon bond formation
Asymmetric carbonβ€”carbon bond formation by phase-transfer catalysis; synthesis of optically active 3-substituted dihydroisocarbostyrils
✍ Toshio Wakabayashi; Kenzo Watanabe πŸ“‚ Article πŸ“… 1978 πŸ› Elsevier Science 🌐 French βš– 133 KB

Recent investigations have demonstrated that phase-transfer catalysis has a considerable potential in synthetic organic chemistry. 1 The alkylation2 of Bdicarbonyl compounds and the Wittig-Homer' reaction of carbonyl compounds have led to interesting results, but no successful examples of reactions