4.7 Article

Catalytic Environmentally Friendly Protocol for Achmatowicz Rearrangement

期刊

JOURNAL OF ORGANIC CHEMISTRY
卷 81, 期 11, 页码 4847-4855

出版社

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.6b00469

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资金

  1. HKUST [R9309]
  2. Research Grant Council of Hong Kong [ECS 605912, GRF 605113, GRF 16305314]
  3. National Natural Science Foundation of China [NSFC 21472160]

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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 (mchlorobenzoic 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.

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