Synthesis 2018; 50(08): 1661-1666
DOI: 10.1055/s-0036-1591751
paper
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Construction of Bridgehead Quaternary Carbon Containing Bicyclo[3.3.1]nonanes by Palladium-Catalyzed ­Desymmetric Arylation

Jinhui Cai
Engineering Research Center of Organosilicon Compounds & Materials, Ministry of Education, College of Chemistry and Molecular Sciences, Wuhan University, 299 Bayi Rd, Wuhan 430072, Hubei, China   Email: wenboliu@whu.edu.cn
,
Qiang Wei
Engineering Research Center of Organosilicon Compounds & Materials, Ministry of Education, College of Chemistry and Molecular Sciences, Wuhan University, 299 Bayi Rd, Wuhan 430072, Hubei, China   Email: wenboliu@whu.edu.cn
,
Xu-Dong Hu
Engineering Research Center of Organosilicon Compounds & Materials, Ministry of Education, College of Chemistry and Molecular Sciences, Wuhan University, 299 Bayi Rd, Wuhan 430072, Hubei, China   Email: wenboliu@whu.edu.cn
,
Yan Zhang
Engineering Research Center of Organosilicon Compounds & Materials, Ministry of Education, College of Chemistry and Molecular Sciences, Wuhan University, 299 Bayi Rd, Wuhan 430072, Hubei, China   Email: wenboliu@whu.edu.cn
,
Weishuang Li
Engineering Research Center of Organosilicon Compounds & Materials, Ministry of Education, College of Chemistry and Molecular Sciences, Wuhan University, 299 Bayi Rd, Wuhan 430072, Hubei, China   Email: wenboliu@whu.edu.cn
,
Hengjiang Cong
Engineering Research Center of Organosilicon Compounds & Materials, Ministry of Education, College of Chemistry and Molecular Sciences, Wuhan University, 299 Bayi Rd, Wuhan 430072, Hubei, China   Email: wenboliu@whu.edu.cn
,
Wei Liu
Engineering Research Center of Organosilicon Compounds & Materials, Ministry of Education, College of Chemistry and Molecular Sciences, Wuhan University, 299 Bayi Rd, Wuhan 430072, Hubei, China   Email: wenboliu@whu.edu.cn
,
Wen-Bo Liu*
Engineering Research Center of Organosilicon Compounds & Materials, Ministry of Education, College of Chemistry and Molecular Sciences, Wuhan University, 299 Bayi Rd, Wuhan 430072, Hubei, China   Email: wenboliu@whu.edu.cn
› Author Affiliations
This work was financially supported by National Natural Science Foundation of China (NSFC 21772148, 21602160).
Further Information

Publication History

Received: 05 December 2017

Accepted: 12 December 2017

Publication Date:
24 January 2018 (online)


Abstract

An enantioselective and catalytic method for the synthesis of bridgehead quaternary carbon containing bicyclo[3.3.1]nonanes is described. The intramolecular desymmetric arylation of α-disubstituted 1,3-diketones was achieved using a chiral Pd/PHOX complex. A variety of bridged cyclic molecules, common skeleton for polyprenylated acylphloroglucinols, were obtained in up to 84% yield with 86% ee.

Supporting Information

 
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