✦ LIBER ✦

Asymmetric synthesis of permethric acid. stereochemistry of chiral copper carbenoid reaction

✍ Scribed by Tadatoshi Aratani; Yukio Yoneyoshi; Tsuneyuki Nagase

Publisher: Elsevier Science
Year: 1982
Tongue: French
Weight: 213 KB
Volume: 23
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)86922-1

No coin nor oath required. For personal study only.

✦ Synopsis

The most effective optical isomer (lR-cis) of permethric acid --(2_, R = H), a potent intermediate in the production of synthetic pyrethroid, was enantioselectively prepared. Certain kinds of cyclopropanecarboxylic acids are useful as acid components of synthetic pyrethroids.' Optically active form of such a compound produces the more selective insecticide, which is more active to the insects and less toxic to the mammals. Among these carboxylic acids are lR-trans-chrysanthemic -acid (1, R = H) and lR-cis-permethric acid,namely 3-(2,2-dichlorovinyl)-2,2---

📜 SIMILAR VOLUMES

Asymmetric synthesis of chrysanthemic ac

Asymmetric synthesis of chrysanthemic acid. An application of copper carbenoid reaction

✍ T. Aratani; Y. Yoneyoshi; T. Nagase 📂 Article 📅 1977 🏛 Elsevier Science 🌐 French ⚖ 198 KB

Chrysanthemic acid (I, R = H) constitutes an acidic component of the pyrethroid, 1 which is effective as an insecticide. Among its four optical isomers, the naturally occurring d-trans isomer has the highest activity.

Asymmetric synthesis of chrysanthemic ac

Asymmetric synthesis of chrysanthemic acid. An application of copper carbenoid reaction

✍ T. Aratani; Y. Yoneyoshi; T. Nagase 📂 Article 📅 1975 🏛 Elsevier Science 🌐 French ⚖ 176 KB

Asymmetric induction was observed in the decomposition of diasoalkanes in the presence of certain chiral copper complexes. 1 We have applied this chiral carbenoid reaction to the synthesis of chrysanthemic acid\* (ea. 1). Systematic studies have been carried out to achieve an optical yield of 60-70$

ChemInform Abstract: New Aspect of Carbe

ChemInform Abstract: New Aspect of Carbenoid Reaction: Exploitation of New Asymmetric Synthesis Using Chiral Carbenoid Species

✍ K. ITOH; T. FUKUDA; H. KITAJIMA; T. KATSUKI 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 27 KB 👁 1 views

Asymmetric Synthesis of Cyclic Ethers by

Asymmetric Synthesis of Cyclic Ethers by Rearrangement of Oxonium Ylides Generated from Chiral Copper Carbenoids

✍ J.Stephen Clark; Mark Fretwell; Gavin A. Whitlock; Christopher J. Burns; David N 📂 Article 📅 1998 🏛 Elsevier Science 🌐 French ⚖ 639 KB

Tetmhydrofumn-3-ones and tetrahydropymrr-3-ones can be prepmedenrmtiosekxtively by rearrangementof the ylide-typeintermediatesgeneratedby the reactionof a chiral copper carbenoidwith the oxygenatom of a pendant allylic ether. Cyclic ethers with enantiomericexcesses of up to 57% have been obtainedusi

Practical Copper-Catalyzed Asymmetric Sy

Practical Copper-Catalyzed Asymmetric Synthesis of Chiral Chrysanthemic Acid Esters

✍ Makoto Itagaki; Katsuhiro Suenobu 📂 Article 📅 2007 🏛 John Wiley and Sons ⚖ 11 KB 👁 1 views

On the Mechanism and Stereochemistry of

On the Mechanism and Stereochemistry of Chiral Lithium-Carbenoid-Promoted Cyclopropanation Reactions

✍ Zhuofeng Ke; Yubing Zhou; Hui Gao; Cunyuan Zhao; David Lee Phillips 📂 Article 📅 2007 🏛 John Wiley and Sons 🌐 English ⚖ 273 KB 👁 1 views

## Abstract An investigation into the mechanism and stereochemistry of chiral lithium‐carbenoid‐promoted cyclopropanation reactions by using density functional theory (DFT) methods is reported. Previous work suggested that this type of cyclopropanation reaction may proceed by competition between a