Palladium‐Catalyzed [4+2] and [6+2] Dipolar Cycloadditions for the Construction of Benzo[d]isothiazole 1,1‐Dioxide Fused 1,3‐Oxazinanes and 1,3‐Oxazocanes

Author:

Chen Lei1,Xie Hongling1,Xue Yu1,Han Zhengyu1,Sun Jianwei2,Huang Hai1

Affiliation:

1. Jiangsu Key Laboratory of Advanced Catalytic Materials & Technology, School of Petrochemical Engineering, Changzhou University Changzhou Jiangsu 213164 China

2. Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay Kowloon, Hong Kong SAR China

Abstract

Comprehensive SummaryThe Pd‐catalyzed dipolar cycloaddition represents a significant synthetic strategy for the construction of useful heterocyclic compounds. This study developed the dipolar [4+2] and [6+2] cycloaddition reactions of benzo[d]isothiazole 1,1‐dioxides (BDs) leading to the synthesis of BD‐fused 1,3‐oxazinane and 1,3‐oxazocane derivatives, respectively. In particular, the synthesis of BD‐fused 1,3‐oxazinanes demonstrated regio‐ and enantioselective characteristics, resulting in products with good yields, enantioselectivity and regioselectivity (if applicable). Furthermore, the [6+2] cycloaddition reaction developed in this work represented the first strategy for the synthesis of medium‐sized ring compounds based on BDs.

Funder

National Natural Science Foundation of China

Publisher

Wiley

Subject

General Chemistry

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