Starting with the aldehydes 7 and methyl vinyl ketone the title compounds 3a-d and their corresponding 2 2 isomers 16a -d are prepared in three steps: 1) thiazolium salt-catalyzed addition reaction to yield the diketone 8, 2) cyclocondensation reaction to give the corresponding cyclopentenone 11, an
Stereocontrolled Synthesis of the Insect Growth Regulators — Alkyl (2E,4E)-Dodecadienoates
✍ Scribed by Nov´k, Lajos ;Roh´ly, J´nos ;Kolonits, P´l ;Fekete, Jenö ;Varjas, Ĺszló ;Sźntay, Csaba
- Book ID
- 102901831
- Publisher
- John Wiley and Sons
- Year
- 1982
- Tongue
- English
- Weight
- 571 KB
- Volume
- 1982
- Category
- Article
- ISSN
- 0947-3440
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✦ Synopsis
Abstract
The title compounds 1 and 16 were synthesized by condensation of the dianions of β‐keto esters 5 and 11 with aldehydes 4, and lithium dialkylcuprate addition to the enol acetate or enol phosphate of unsaturated β‐keto esters 8 and 15. The (2__E__,4__E__)‐dodecadienoate derivatives 1 and 16 were formed in a stereoselective manner.
📜 SIMILAR VOLUMES
Thermal treatment of p-allenic esters (2) with alumina catalyst in aprotic solvents yielded (2E,&Z)-dienoic esters (3) in 57-87s yields with 91-100% stereoselectivity. p-Allenic esters 2, which are readily obtained from trialkyl orthoacetate and propargylic alcohols (I.)', can be converted to 2,4-di
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