Pd(ii)-Catalyzed aerobic 1,2-difunctionalization of conjugated dienes: efficient synthesis of morpholines and 2-morpholones

A novel and efficient methodology concerning the Pd(ii)-catalyzed intermolecular difunctionalization of conjugated dienes is reported to synthesize a series of functionalized morpholines and 2-morpholones. Widely distributed and easily obtained β-amino alcohols and α-amino acids, as starting nitroge...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2018, Vol.16 (31), p.5618-5625
Main Authors: Wen, Ke, Wu, Zhengxing, Chen, Buyun, Chen, Jianzhong, Zhang, Wanbin
Format: Article
Language:English
Subjects:
Alcohols
Amino acids
Chemical synthesis
Dienes
Genetic transformation
Oxygen
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Summary:A novel and efficient methodology concerning the Pd(ii)-catalyzed intermolecular difunctionalization of conjugated dienes is reported to synthesize a series of functionalized morpholines and 2-morpholones. Widely distributed and easily obtained β-amino alcohols and α-amino acids, as starting nitrogen and oxygen sources, are successfully applied in the difunctionalization of conjugated dienes respectively. The majority of the desired products were obtained in moderate to excellent yields. Oxygen was successfully employed as a terminal oxidant. Further transformation of the generated products allowed for the expansion of structural diversity.
ISSN:1477-0520
1477-0539
DOI:10.1039/c8ob01291a