Organic Letters p. 7053 - 7056 (2018)
Update date:2022-08-02
Topics:
Zheng, Limeng
Zhou, Bingwei
Jin, Hongwei
Li, Ting
Liu, Yunkui
A radical-triggered tandem cyclization of 1,6-enynes has been developed herein. Strained 1H-cyclopropa[b]naphthalene-2,7-diones are successfully obtained in moderate to good yields with excellent stereoselectivity. Mechanistic studies reveal a key role of water in generating a hydroxyl radical that initiates a sequential Michael addition/ring closure pathway. Importantly, the formed hydroxyl is proposed to be a good leaving group during the cyclopropane ring formation.
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Doi:10.1016/S0040-4039(00)97858-4
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(2021)
