Synthesis of chiral 3E,5E-octadiene-1,2R-7R,8-tetraol frameworks by means of palladium(II)-promoted hetero-Claisen rearrangement: Mechanistic aspect

DOI: 10.1016/0040-4020(96)00854-X

Source and publish data:

Tetrahedron p. 13919 - 13932 (1996)

Update date:2022-08-03

Topics:

Authors:

Saito, Seiki

Kuroda, Akiyoshi

Matsunaga, Hiroshi

Ikeda, Shushiro

Read Full Text PDF DownLoad Join now for total 90,000,000 free articles

Article abstract of DOI:10.1016/0040-4020(96)00854-X

A plausible mechanism has been proposed for the exclusive formation of symmetrical dienediol such as 1,6-bis(acetoxy)-2,4-diene in palladium(II)-promoted [3,3]sigmatropic rearrangement of 3,4-bis(acetoxy)-1,5-diene system. This mechanism referred to as migration-induced intramolecular dioxanium ion switching (MIDIS) process can reasonably explain why the vicinal acetoxy groups move from 3,4-position and not to 5,6- but two directionally to 1,6-position.

Full text of DOI:10.1016/0040-4020(96)00854-X

Products guided by the article

Product name:(E)-3-{(4S,5S)-5-[(E)-3-(4-Methoxy-benzyloxy)-propenyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-prop-2-en-1-ol

Cas No:185025-14-3

R&D Labs maybe for 185025-14-3

zhenjiang runjing high purity chemical co ltd

Contact:+86-511-83361155

Address:No.8.haixi road,international chemical park
Beijing Wisdom Chemicals Co., Ltd.

Contact:+86-10-52350335

Address:F2, BLDG 19, Liando Valley U, Majuqiao, Tongzhou District, Beijing, China
HANGZHOU PANYU CHEMICAL CO.,LIMITED

Contact:+86-571-86578491

Address:Rm 605, NO.1870 Binsheng Road,Binjiang Dist, Hangzhou, China
NanJing KaiHeng Chemical CO., LTD.

Contact:+86-25-85768391

Address:RM.1704, D, WANDA PLAZA, NO.110, MIDDLE JIANGDONG ROAD, NANJING, CHINA
qingdao goldenchem imp and exp co.,ltd.

Contact:532-55579246

Address:no.62 ,haier road laoshan distirct

Relevant to this article

Highly selective, novel analogs of 4-[2-(diphenylmethoxy)ethyl]-1- benzylpiperidine for the dopamine transporter: Effect of different aromatic substitutions on their affinity and selectivity

Doi:10.1021/jm960638e
(1997)
Doi:10.1021/ja01144a510
(1952)
Aggregative activation and carbanion chemistry: Complex base deprotonation and directed functionalisation of dithioacetals

Doi:10.1016/S0040-4020(96)00972-6
(1996)
Retropane - A new rhenium complex as a potential ligand to label the dopamine transporter

Doi:10.1016/S0960-894X(96)00533-1
(1996)
Baeyer-Villiger oxidation of 6-oxotricyclo-[3.2.1.0^2,7]octanes; Regioselective opening of push-pull substituted cyclopropanes

Doi:10.1055/s-1997-1273
(1997)
Macropolyhedral boron-containing cluster chemistry: Nineteen-vertex [(PPh₃)NiS₂B₁₆H₁₂(PPh₃)] and eighteen-vertex S₂B₁₆H₁₄(PPh₃)

Doi:10.1039/dt9960004155
(1996)

Article Doi