Electron-rich benzofulvenes as effective dipolarophiles in copper(i)-catalyzed asymmetric 1,3-dipolar cycloaddition of azomethine ylides

Chang，Xin1,2; Liu，Xue Tao1,2; Li，Fangfang3; Yang，Yuhong3; Chung，Lung Wa3; Wang，Chun Jiang1,2

2023

10.1039/d3sc00435j

Chemical Science   影响因子和分区

2041-6520

2041-6539

A series of benzofulvenes without any electron-withdrawing substituents were employed as 2π-type dipolarophiles for the first time to participate in Cu(i)-catalyzed asymmetric 1,3-dipolar cycloaddition (1,3-DC) reactions of azomethine ylides. An intrinsic non-benzenoid aromatic characteristic from benzofulvenes serves as a key driving force for activation of the electron-rich benzofulvenes. Utilizing the current methodology, a wide range of multi-substituted chiral spiro-pyrrolidine derivatives containing two contiguous all-carbon quaternary centers were formed in good yield with exclusive chemo-/regioselectivity and high to excellent stereoselectivity. Computational mechanistic studies elucidate the origin of the stereochemical outcome and the chemoselectivity, in which the thermostability of these cycloaddition products is the major factor.

SCI ; EI ; IC ; CCR

英语

NI论文

通讯

NSFC["22071186","22101216","22073067","21933003","22193020","22193023"] ; Hubei Province Natural Science Foundation[2020CFA036] ; China Postdoctoral Science Foundation[2021M702514] ; Fundamental Research Funds for the Central Universities[2042022kf1180] ; Shenzhen Nobel Prize Scientists Laboratory Project[C17783101] ; Guangdong Provincial Key Laboratory of Catalytic Chemistry[2020B121201002]

Chemistry

Chemistry, Multidisciplinary

WOS:001008464900001

ROYAL SOC CHEMISTRY

20231914076950

Copper compounds

Chemical Reactions:802.2

2-s2.0-85158009337

Scopus

1.Engineering Research Center of Organosilicon Compounds & Materials,Ministry of Education,College of Chemistry and Molecular Sciences,Wuhan University,Wuhan,430072,China
2.State Key Laboratory of Organometallic Chemistry,Shanghai Institute of Organic Chemistry,Shanghai,230021,China
3.Department of Chemistry and Guangdong Provincial Key Laboratory of Catalysis,Southern University of Science and Technology,Shenzhen,518055,China

Chang，Xin,Liu，Xue Tao,Li，Fangfang,et al. Electron-rich benzofulvenes as effective dipolarophiles in copper(i)-catalyzed asymmetric 1,3-dipolar cycloaddition of azomethine ylides[J]. Chemical Science,2023,14(20):5460-5469.

Chang，Xin,Liu，Xue Tao,Li，Fangfang,Yang，Yuhong,Chung，Lung Wa,&Wang，Chun Jiang.(2023).Electron-rich benzofulvenes as effective dipolarophiles in copper(i)-catalyzed asymmetric 1,3-dipolar cycloaddition of azomethine ylides.Chemical Science,14(20),5460-5469.

Chang，Xin,et al."Electron-rich benzofulvenes as effective dipolarophiles in copper(i)-catalyzed asymmetric 1,3-dipolar cycloaddition of azomethine ylides".Chemical Science 14.20(2023):5460-5469.