Ni(II)-Catalyzed enantioselective Mukaiyama-Mannich reaction between silyl enol ethers and cyclic N-sulfonyl α-ketiminoesters

作者：Xie, Lei; Ma, Hongli; Li, Jiaqi; Yu, Yuan; Qin, Zhaohai; Fu, Bin^*

来源：Organic Chemistry Frontiers, 2017, 4(9): 1858-1862.

DOI：10.1039/c7qo00370f

• FRIEDEL-CRAFTS ALKYLATION
• QUATERNARY CARBON STEREOCENTERS
• STEREOSELECTIVE-SYNTHESIS
• ASYMMETRIC ADDITION
• CHIRAL BENZOSULTAMS
• SULTAM AUXILIARIES
• ARYLBORONIC ACIDS
• MICHAEL ADDITION
• FUSED AZIRIDINES
• IN-VITRO

The enantioselective Mukaiyama-Mannich reaction of cyclic N-sulfonyl alpha-ketiminoesters and silyl enol ethers was realized for the first time using a Ni(II)-bis(oxazoline) complex. Both di-and tri-substituted silyl enol ethers as well as silyl dienol ethers generated from the corresponding aromatic ketones or alpha, beta-unsaturated ketones were well tolerated in this reaction. The reaction proceeded smoothly under mild conditions to provide a series of enantioenriched benzofused sultams containing an alpha-quaternary alpha-amino ester and an aromatic ketone moiety. Moreover, the products can be readily converted into potentially bioactive benzosultams including aziridine and polycyclic benzosultams.

• 出版日期2017-9-1
• 单位中国农业大学