Phosphine-Catalyzed (3+2) Annulation of Isoindigos with Allenes: Enantioselective Formation of Two Vicinal Quaternary Stereogenic Centers

Chan，Wai Lun1; Tang，Xiaodong1,2; Zhang，Fuhao1,3; Quek，Glenn1; Mei，Guang Jian1; Lu，Yixin1,2

2019-05-06

10.1002/anie.201900758

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION   影响因子和分区

1433-7851

1521-3773

Construction of contiguous all-carbon quaternary stereogenic centers is a long-standing challenge in synthetic organic chemistry. In this report, a phosphine-catalyzed enantioselective (3+2) annulation reaction between allenes and isoindigos, containing either two identical or different oxindole moieties, is introduced as a powerful strategy for the construction of spirocyclic bisindoline alkaloid core structures. The reported reactions feature high chemical yields, excellent enantioselectivities, and very good regioselectivities, and are highly useful for creating structurally challenging bisindoline natural products.

alkaloids allenes annulations organocatalysis spiro compounds

SCI ; EI ; IC ; CCR

英语

NI期刊

其他

National Natural Science Foundation of China[21672158] ; National University of Singapore[R-143-000-695-114] ; National Research Foundation Singapore[R-143-000-A15-281]

WOS:000471976400019

Wiley-VCH Verlag

20191006594035

Alkaloids ; Catalysis ; Hydrocarbons ; Metabolites ; Phosphorus compounds

Physical Chemistry:801.4 ; Chemical Reactions:802.2 ; Chemical Products Generally:804 ; Organic Compounds:804.1

CHEMISTRY

2-s2.0-85062335418

Scopus

1.Department of ChemistryNational University of Singapore,Singapore,3 Science Drive 3,117543,Singapore
2.National University of Singapore (Suzhou) Research Institute,Suzhou,377 Lin Quan Street, Suzhou Industrial Park,215123,China
3.Department of ChemistrySouthern University of Science and Technology,Shenzhen,518000,China

Chan，Wai Lun,Tang，Xiaodong,Zhang，Fuhao,et al. Phosphine-Catalyzed (3+2) Annulation of Isoindigos with Allenes: Enantioselective Formation of Two Vicinal Quaternary Stereogenic Centers[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2019,58(19):6260-6264.

Chan，Wai Lun,Tang，Xiaodong,Zhang，Fuhao,Quek，Glenn,Mei，Guang Jian,&Lu，Yixin.(2019).Phosphine-Catalyzed (3+2) Annulation of Isoindigos with Allenes: Enantioselective Formation of Two Vicinal Quaternary Stereogenic Centers.ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,58(19),6260-6264.

Chan，Wai Lun,et al."Phosphine-Catalyzed (3+2) Annulation of Isoindigos with Allenes: Enantioselective Formation of Two Vicinal Quaternary Stereogenic Centers".ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 58.19(2019):6260-6264.