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Highly Enantioselective Construction of Dihydrooxazines via Pd-Catalyzed Asymmetric Carboetherification

Na Li, Baozhen Sun, Shuang Liu, Jinbo Zhao* and Qian Zhang

*Department of Chemistry, Key Laboratory of Functional Molecule Design and Synthesis of Jilin Province, Northeast Normal University, Changchun, 130024, P. R. China, Email: zhaojb100nenu.edu.cn

N. Li, B. Sun, S. Liu, J. Zhao, Q. Zhang, Org. Lett., 2020, 22, 190-193.

DOI: 10.1021/acs.orglett.9b04123 (free Supporting Information)



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Abstract

Pd-catalyzed asymmetric carboetherification of γ,δ-alkenyl oximes with (hetero)aryl and alkenyl halides in the presence of (R)-DTBM-SegPhos(O) and Pd(dba)2 enables a straightforward synthesis of highly enantioenriched 5,6-dihydro-4H-1,2-oxazines. Alternatively, commercially available (R)-DTBM-SegPhos can be oxidized in situ in the presence of water and Pd(OAc)2 without erosion of enantiocontrol.

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Key Words

N-heterocycles, O-heterocycles


ID: J54-Y2020