Organocatalytic enantioselective reaction of tertiary alpha-(7-indolyl)methanols with tryptamines

Yue, Zhibin1; Shen, Boming2; Cao, Jie1; Chen, Xuling2; Fang, Fang2; Li, Pengfei2; Yu, Peiyuan2; Li, Wenjun1

2023-06-01

10.1039/d3qo00577a

ORGANIC CHEMISTRY FRONTIERS   影响因子和分区

2052-4129

With the aid of chiral phosphoric acid, enantioselective 1,6-addition of tryptamines to in situ formed alkynyl 7-methylene-7H-indoles from tertiary alpha-(7-indolyl)methanols has been established for the first time, furnishing a broad range of axially chiral tetrasubstituted allenes featuring indole and hexahydropyrrolo[2,3-b]indole units in good to high yields and with asymmetric induction. DFT calculations have been carried out to shed light on the reaction mechanism and to understand the origin of stereoselectivity. Importantly, this protocol not only enriches the chemistry of alpha-(7-indolyl)methanols but also provides an efficient means for the preparation of structurally diverse axially chiral tetrasubstituted allenes.

SCI ; EI ; IC

英语

通讯

Natural Science Foundation of Shandong Province[ZR2021MB026] ; Special Funds of the Taishan Scholar Program of Shandong Province[tsqn201812047] ; Guangdong Innovative Program[2019BT02Y335] ; Guangdong Provincial Key Laboratory of Catalysis[2020B121201002] ; Shenzhen Higher Education Institution Stable Support Plan[20200925152921001]

Chemistry

Chemistry, Organic

WOS:001010291800001

ROYAL SOC CHEMISTRY

20232714346582

Enantioselectivity ; Polycyclic aromatic hydrocarbons ; Stereochemistry

Chemistry:801 ; Physical Chemistry:801.4 ; Organic Compounds:804.1

Web of Science

1.Qingdao Univ, Sch Pharm, Dept Med Chem, Qingdao 266021, Shandong, Peoples R China
2.Southern Univ Sci & Technol SUSTech, Guangming Adv Res Inst, Coll Sci, Dept Chem,Guangdong Prov Key Lab Catalysis, Shenzhen 518055, Guangdong, Peoples R China

Yue, Zhibin,Shen, Boming,Cao, Jie,et al. Organocatalytic enantioselective reaction of tertiary alpha-(7-indolyl)methanols with tryptamines[J]. ORGANIC CHEMISTRY FRONTIERS,2023,10(14):3662-3668.

Yue, Zhibin.,Shen, Boming.,Cao, Jie.,Chen, Xuling.,Fang, Fang.,...&Li, Wenjun.(2023).Organocatalytic enantioselective reaction of tertiary alpha-(7-indolyl)methanols with tryptamines.ORGANIC CHEMISTRY FRONTIERS,10(14),3662-3668.

Yue, Zhibin,et al."Organocatalytic enantioselective reaction of tertiary alpha-(7-indolyl)methanols with tryptamines".ORGANIC CHEMISTRY FRONTIERS 10.14(2023):3662-3668.