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Iron‐Catalyzed Asymmetric Inter‐ and Intramolecular Aerobic Oxidative Dearomatizing Spirocyclization of 2‐Naphthols
Asian Journal of Organic Chemistry ( IF 2.7 ) Pub Date : 2019-12-10 , DOI: 10.1002/ajoc.201900602
Takuya Oguma 1 , Daiki Doiuchi 1 , Chisaki Fujitomo 1 , Chungsik Kim 2 , Hiroki Hayashi 3 , Tatsuya Uchida 2, 3 , Tsutomu Katsuki 2
Affiliation  

Highly chemo‐ and enantioselective inter‐ and intra‐molecular oxidative dearomatizing spirocyclization of 1‐alkyl‐2‐naphthols with O2 as the hydrogen acceptor was achieved using an iron catalyst. In the iron complex 1‐catalyzed reaction, 1‐methyl‐2‐naphthols 2 in the presence of phenol derivatives as the nucleophile was selectively oxidized, producing the spirocyclic ketones with good to high enantioselectivities via a tandem strategy. Pre‐synthesized 1,1′‐methylbis(arenol)s 6 and 7, intermediates of the tandem strategy were also converted to the desired products with chemo‐ and enantioselectivity.

中文翻译:

铁催化2-萘酚的不对称分子间和分子内好氧氧化脱芳香化螺旋环化

使用铁催化剂,以O 2为氢受体,高度化学和对映选择性分子间和分子内氧化脱芳香化螺环化了1烷基-2-萘酚。在铁络合物1催化的反应中,在苯酚衍生物作为亲核试剂的存在下,1-甲基-2-萘2被选择性地氧化,通过串联策略产生具有良好至高对映选择性的螺环酮。预先串联的1,1'-甲基双(芳烯醇)67中间体,也已通过化学和对映体选择性转化为所需的产物。
更新日期:2019-12-11
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