Citation: Wang Lin, Yang Lili, Ou Yunfu, Xu Shihai, Lin Qifu, Yang Dingqiao. Platinum-Catalyzed syn-Stereocontrolled Ring-Opening of Oxabicyclic Alkenes with Arylsulfonyl Hydrazides[J]. Chinese Journal of Organic Chemistry, ;2020, 40(12): 4228-4236. doi: 10.6023/cjoc202006074 shu

Platinum-Catalyzed syn-Stereocontrolled Ring-Opening of Oxabicyclic Alkenes with Arylsulfonyl Hydrazides

  • Corresponding author: Xu Shihai, txush@jnu.edu.c Yang Dingqiao, yangdq@scnu.edu.cn
  • 共同第一作者(These authors contributed equally to this work).
  • Received Date: 30 June 2020
    Revised Date: 23 July 2020
    Available Online: 18 August 2020

    Fund Project: Project supported by the National Natural Science Foundation of China (Nos. 21672084, 21372090) and the Special Fund Project of Department of Natural Resources of Guangdong Province (Guangdong Natural Resources Cooperation) (No. 2020037)the National Natural Science Foundation of China 21672084the Special Fund Project of Department of Natural Resources of Guangdong Province (Guangdong Natural Resources Cooperation) 2020037the National Natural Science Foundation of China 21372090

Figures(3)

  • A platinum-catalyzed syn-stereocontrolled ring-opening reaction of oxabicyclic alkenes with arylsulfonyl hydrazides was developed. This protocol exhibited high efficiency and good functional group tolerance, affording cis-2-aryl-1, 2-dihydronaphthalen-1-ols (3) or 2-aryl-naphthalenes (4) as dehydrated products in good to excellent yields under mild conditions (up to 89%). In addition, the cis-1, 2-configuration of product (1S*, 2R*)-6, 7-dibromo-2-(p-tolyl)-1, 2-dihydronaphthalen-1-ol (3db) was confirmed by X-ray single crystal diffraction analysis. Based on the results, a plausible mechanism for the ring-opening reaction was proposed. Remarkably, arylsulfonyl hydrazides were used as carboanion nucleophiles in the ring-opening reaction via releasing N2 and SO2 in situ.
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