Acyclic stereocontrol via asymmetric [2,3]-Wittig rearrangement with high enantio- and erythro-selectivity and its use in the chiral synthesis of insect pheromones
✍ Scribed by Noboru Sayo; Ken-ichi Azuma; Kōichi Mikami; Takeshi Nakai
- Publisher
- Elsevier Science
- Year
- 1984
- Tongue
- French
- Weight
- 243 KB
- Volume
- 25
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
Such an asymmetric [2,3]-Wittig variant that is both highly enantio-and erythroselective is described within the context of the chiral synthesis of the insect pheromones, (35, 4S)-4-methyl-3-heptanol and (S)-4-methyl-3-heptanone. The control of both diastereo-and enantioselection during carbon-carbon bond formations is of great importance in synthesis. Recently several asymmetric aldol-type reactions have reached impressive levels of success.' As part of a program designed to develop the [2,3]-Wittig sigmatropic rearrangement into a new, basic strategy for acyclic stereocontrol,' we have