Complete control of the rearrangement modes of enolates of. alpha.-allyloxy ketones: reversal from the [3, 3]-Claisen to the [2, 3]-Wittig pathway by the use of the …
JI Luengo, M Koreeda
Index: Luengo, Juan I.; Koreeda, Masato Journal of Organic Chemistry, 1989 , vol. 54, # 23 p. 5415 - 5417
Full Text: HTML
Citation Number: 7
Abstract
Summary: It has been shown that the predilection for the [3, 3]-Claisen rearrangement pathway of enolates of a-allyloxy ketones is cleanly overridden by the [2, 3]-Wittig rearrangement route with the use of carbanions of their corresponding N, N- dimethylhydrazones. Since the formation of these hydrazones as well as hydrolysis of the rearranged a-hydroxyhydrazones can be readily achieved, this approach allows a [2, 3]- ...
Related Articles:
Indium-mediated allylation of 1, 2-diketones
[Kang, Suk-Ku; Baik, Tae-Gon; Jiao, Xiang-Hua Synthetic Communications, 2002 , vol. 32, # 1 p. 75 - 78]
[Takuwa, Akio; Nishigaichi, Yutaka; Yamashita, Koichi; Iwamoto, Hidetoshi Chemistry Letters, 1990 , # 9 p. 1761 - 1764]