Amine-promoted three-component cycloaddition of bicyclo[1.1.0]butanes with hydroxylamine and polyformaldehyde: expedient access to 2-oxa-3-azabicyclo[3.1.1]heptanes†
Yu Zhu , Xueli Lv , Jun Hong , Shengxing Wu , Zhi Li , Minyan Wang , Xinpeng Jiang
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引用次数: 0
Abstract
Bicyclo[3.1.1]heptanes are generally considered important bioisosteres for meta-substituted arenes. Herein, we have developed an amine-promoted synthesis of C4-unsubstituted 2-oxa-3-azabicyclo[3.1.1]heptanes via a formal dipolar [4π + 2σ] cycloaddition of bicyclo[1.1.0]butanes (BCBs) with nitrones generated in situ from hydroxylamines and polyformaldehyde. This synthesis featured mild reaction conditions with excellent functional group tolerance. Notably, mono-substituted and disubstituted BCBs exhibited different regioselectivities during cycloaddition reactions. Computational density functional theory (DFT) calculations provided insights into the mechanistic aspects of this selective cycloaddition, further highlighting the potential of this synthetic approach.
期刊介绍：
Green Chemistry is a journal that provides a unique forum for the publication of innovative research on the development of alternative green and sustainable technologies. The scope of Green Chemistry is based on the definition proposed by Anastas and Warner (Green Chemistry: Theory and Practice, P T Anastas and J C Warner, Oxford University Press, Oxford, 1998), which defines green chemistry as the utilisation of a set of principles that reduces or eliminates the use or generation of hazardous substances in the design, manufacture and application of chemical products. Green Chemistry aims to reduce the environmental impact of the chemical enterprise by developing a technology base that is inherently non-toxic to living things and the environment. The journal welcomes submissions on all aspects of research relating to this endeavor and publishes original and significant cutting-edge research that is likely to be of wide general appeal. For a work to be published, it must present a significant advance in green chemistry, including a comparison with existing methods and a demonstration of advantages over those methods.
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