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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
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  • Lei Chen,
  • Hongling Xie,
  • Yu Xue,
  • Zhengyu Han,
  • Jianwei Sun,
  • Hai Huang
Lei Chen
Changzhou University
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Hongling Xie
Changzhou University
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Yu Xue
Changzhou University
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Zhengyu Han
Changzhou University
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Jianwei Sun
The Hong Kong University of Science and Technology
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Hai Huang
Changzhou University

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Abstract

The Pd-catalyzed dipolar cycloaddition represents a significant synthetic strategy for the construction of useful heterocyclic com-pounds. 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 strat-egy for the synthesis of medium-sized ring compounds based on BDs.
09 Nov 2023Reviewer(s) Assigned