Diastereodivergent formal [4 + 1] cycloaddition of azoalkenes as one-carbon synthons

Autor: Chun-Yan Guan, Tian-Jiao Han, Shi-Kun Jia, Yuan-Zhao Hua, Guang-Jian Mei
Jazyk: angličtina
Rok vydání: 2023
Předmět:
Zdroj: Green Synthesis and Catalysis, Vol 4, Iss 3, Pp 258-262 (2023)
Druh dokumentu: article
ISSN: 2666-5549
DOI: 10.1016/j.gresc.2022.05.003
Popis: The first diastereodivergent formal [4 ​+ ​1] cycloaddition reactions of azoalkenes with p-quinone methides (p-QMs) have been accomplished. The reported reaction occurred via a domino oxa-1,4-addition/1,6-addition process, allowing the use of common azoalkenes as C1 synthons. A broad range of 2,3-dihydrobenzofurans was smoothly prepared in good yields and with reversible diastereoselectivities. The steric hindrance and hydrogen-bonding interaction were proposed to account for the two different modes of diastereo-control. The projected reaction features the employment of azoalkene as carbene-like C1 synthon, mild conditions, broad substrate scope and tunable diastereoselectivity.
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