Enantioselective Intramolecular Dearomative Lactonization of Naphthols Catalyzed by Planar Chiral Iodoarene

Yang Wang; Cun-Yuan Zhao; Yi-Ping Wang; Wen-Hua Zheng

doi:10.1055/s-0037-1611902

Synthesis, Inhaltsverzeichnis

Synthesis 2019; 51(19): 3675-3682
DOI: 10.1055/s-0037-1611902

paper

Enantioselective Intramolecular Dearomative Lactonization of Naphthols Catalyzed by Planar Chiral Iodoarene

Yang Wang

,

Cun-Yuan Zhao

,

Yi-Ping Wang

,

Wen-Hua Zheng ∗

State Key Laboratory of Coordination Chemistry, Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210023, P. R. of China eMail: wzheng@nju.edu.cn

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Abstract

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Abstract

A series of planar chiral iodoarenes based on [2.2]paracyclophane was synthesized. An efficient asymmetric intramolecular oxidative lactonization of naphthols enabled by a combination of these chiral iodoarenes and mCPBA as oxidant is reported. This reaction proceeds under mild conditions, allowing the formation of spirolactones bearing a tetrasubstituted stereocenter in moderate yields and good enantioselectivity.

Key words

hypervalent iodine catalysis - [2.2]paracyclophane - planar chirality - asymmetric dearomatization - oxidative lactonization

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Referenzen

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