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Diastereoselective Palladium-Catalyzed [4+1] Cycloadditions of 4-Vinyl-1,4-dihydro-2H-3,1-benzoxazin-2-ones with In Situ Formed Carbenes

Yan-Hua Ma*, Fan-Xiao Meng*, Ruo-Nan Wang, Ya-Xin Fan, Qing-Qiang Su, Ji-Yuan Du*

*College of Chemistry and Chemical Engineering, Liaocheng University, Liaocheng, Shandong 252059, P. R. of China, Email: dujy2015163.com, mayanhualcu.edu.cn

Y.-H. Ma, F.-X. Meng, R.-N. Wang, Y.-X. Fan, Q.-Q. Su, J.-Y. Du, Synthesis, 2022, 54, 499-505.

DOI: 10.1055/a-1561-5557


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Abstract

A palladium-catalyzed tandem [4+1] cycloaddition of 4-vinyl-1,4-dihydro-2H-3,1-benzoxazin-2-ones with N-tosyl­hydrazones provides diverse indolines with broad functional group compatibility in good yields with high levels of diastereoselectivity under mild conditions.


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Key Words

aza-o-quinone methides, dihydroindoles, [4+1] cyclo­additions, Pd(0)-catalyzed, benzoxazinones, carbenes


ID: J66-Y2022