Direct Access to Cumbersome Aminated Quaternary Centers by Hyperbaric Aza-Michael Additions

作者：Rulev Alexander Yu; Azad Saleha; Kotsuki Hiyoshizo; Maddaluno Jacques^*

来源：European Journal of Organic Chemistry, 2010, 2010(33): 6423-6429.

DOI：10.1002/ejoc.201000984

• Michael addition
• High-pressure chemistry
• Chirality
• Amines

The aza-Michael addition of secondary amines to alpha,beta- or beta,beta-disubstituted alpha,beta-unsaturated esters was efficiently achieved under high pressure (10-16 kbar) in protic solvents in the absence of any catalyst. The expected cumbersome beta-aminoesters bearing a tertiary amine directly connected to a quaternary carbon atom could be isolated in fair to good yields. By using alpha,beta,gamma,delta-unsaturated esters (alkyl sorbate), the addition took place regioselectively in a 1,6 manner and afforded the beta,gamma-unsaturated delta-aminoesters.

• 出版日期2010-11