190003-03-3Relevant academic research and scientific papers
Chiral lewis base catalyzed highly enantioselective reduction of N-alkyl β-enamino esters with trichlorosilane and water
Wu, Xinjun,Li, Yang,Wang, Chao,Zhou, Li,Lu, Xiaoxia,Sun, Jian
supporting information; experimental part, p. 2846 - 2848 (2011/04/24)
First, test the water! In the presence of a chiral Lewis base catalyst 2, the supposedly moisture-unfriendly reduction system with trichlorosilane was found to be highly efficient and enantioselective when using water as an additive. For the first time, this method enables the reduction of a broad range of N-alkyl β-enamino esters 1 to give N-alkyl β-amino esters 3 in good to high yields and with excellent enantioselectivities (see scheme).
Triclorosilane-mediated stereoselective synthesis of β-amino esters and their conversion to highly enantiomerically enriched β-lactams
Guizzetti, Stefania,Benaglia, Maurizio,Bonsignore, Martina,Raimondi, Laura
, p. 739 - 743 (2011/04/22)
A highly stereoselective trichlorosilane-mediated reduction of N-benzyl enamines was developed; the combination of a low cost, easy to make metal-free catalyst and an inexpensive chiral auxiliary allowed to perform the reaction on substrates with different structural features often with total control of the stereoselectivity. By easy deprotection through hydrogenolysis followed by conversion of β-aminoester to 2-azetidinones, the synthesis of enantiomerically pure β-lactams (>98% e.e.) was successfully accomplished.
Chiral ligand-controlled asymmetric conjugate addition of lithium amides to enoates
Doi, Hirohisa,Sakai, Takeo,Iguchi, Mayu,Yamada, Ken-ichi,Tomioka, Kiyoshi
, p. 2886 - 2887 (2007/10/03)
The external chiral ligand-controlled asymmetric conjugate addition reaction of lithium amides with α,β-unsaturated esters provided β-amino esters in high yields and high enantioselectivities. Copyright
