Tetrahedron

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

S Saito, A Kuroda, H Matsunaga, S Ikeda

文献索引：Saito, Seiki; Kuroda, Akiyoshi; Matsunaga, Hiroshi; Ikeda, Shushiro Tetrahedron, 1996 ,  vol. 52,  # 44  p. 13919 - 13932

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被引用次数: 14

摘要

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 not to 5, 6-but two- ...