Catalytic Environmentally Friendly Protocol for Achmatowicz Rearrangement
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- 作者：Zhilong Li ; Rongbiao Tong
- 刊名：Journal of Organic Chemistry
- 出版年：2016
- 出版时间：June 3, 2016
- 年：2016
- 卷：81
- 期：11
- 页码：4847-4855
- 全文大小：498K
- 年卷期：0
- ISSN：1520-6904
文摘
The increasing interest in Achmatowicz rearrangement in organic synthesis calls for a more environmentally friendly protocol since the most popular oxidants m-CPBA and NBS produced stoichiometric organic side product (m-chlorobenzoic acid or succinimide). Mechanism-guided analysis enables us to develop a new catalytic method (Oxone/KBr) for AchR in excellent yield with K2SO4 as the only side product, which greatly facilitates the purification. This protocol was integrated with other transformations, leading to a rapid access to the highly functionalized dihydropyranones.