Breaking aziridines to construct morpholines with a gold(i)-catalyzed tandem ring-opening and cycloisomerization reaction.
A convenient synthetic method for the construction of morpholine derivatives from easily available aziridines and propargyl alcohols has been successfully developed. A tandem nucleophilic ring-opening of aziridine/6-exo-dig cyclization/double bond isomerization sequence was achieved by using a single gold(i) catalyst under mild conditions. The gold(i) catalyst served as a π acid and also a σ acid to realize the dual activation of both reactants in this reaction. The obtained unsaturated morpholine products could be easily hydrogenated to achieve target morpholine derivatives with good diastereoselectivities in high yields.
Key Lab for Colloid and Interface Chemistry of Education Ministry, School of chemistry and Chemical Engineering, Shandong University, Jinan 250100, People's Republic of China. xuzh@sdu.edu.cn.
Shuyao
S
Zhang
Key Lab for Colloid and Interface Chemistry of Education Ministry, School of chemistry and Chemical Engineering, Shandong University, Jinan 250100, People's Republic of China. xuzh@sdu.edu.cn.
Chuan
C
Shan
Key Lab for Colloid and Interface Chemistry of Education Ministry, School of chemistry and Chemical Engineering, Shandong University, Jinan 250100, People's Republic of China. xuzh@sdu.edu.cn.
Shuai
S
Zhang
Key Lab for Colloid and Interface Chemistry of Education Ministry, School of chemistry and Chemical Engineering, Shandong University, Jinan 250100, People's Republic of China. xuzh@sdu.edu.cn.
Luye
L
Yuan
Key Lab for Colloid and Interface Chemistry of Education Ministry, School of chemistry and Chemical Engineering, Shandong University, Jinan 250100, People's Republic of China. xuzh@sdu.edu.cn.
Jianwu
J
Wang
Key Lab for Colloid and Interface Chemistry of Education Ministry, School of chemistry and Chemical Engineering, Shandong University, Jinan 250100, People's Republic of China. xuzh@sdu.edu.cn.
Chen-Ho
CH
Tung
Key Lab for Colloid and Interface Chemistry of Education Ministry, School of chemistry and Chemical Engineering, Shandong University, Jinan 250100, People's Republic of China. xuzh@sdu.edu.cn.
Ling-Bao
LB
Xing
Key Lab for Colloid and Interface Chemistry of Education Ministry, School of chemistry and Chemical Engineering, Shandong University, Jinan 250100, People's Republic of China. xuzh@sdu.edu.cn and State Key Laboratory of Organometallic Chemistry Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, PR China.
Zhenghu
http://orcid.org/0000-0002-3189-0777
Z
Xu
D001388:Aziridines / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D006046:Gold / Q000737:chemistry*; D007536:Isomerism; D008958:Models, Molecular; D008968:Molecular Conformation; D009025:Morpholines / Q000737:chemistry*
D001388:Aziridines; D009025:Morpholines; C033132:aziridine; D006046:Gold