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: zhaojb100
nenu.edu.cn
N. Li, B. Sun, S. Liu, J. Zhao, Q. Zhang, Org. Lett., 2020, 22, 190-193.
DOI: 10.1021/acs.orglett.9b04123
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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
