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Synthesis 2019; 51(19): 3675-3682
DOI: 10.1055/s-0037-1611902
paper
© Georg Thieme Verlag Stuttgart · New York

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
› Author AffiliationsFinancial support from the National Natural Science Foundation of China (21772086), the Fundamental Research Funds for the Central Universities (020514380118), and Nanjing University is gratefully acknowledged (W.-H.Z.).
Further Information

Publication History

Received: 27 May 2019

Accepted after revision: 09 July 2019

Publication Date:
05 August 2019 (online)

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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

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1611902.
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