190003-04-4Relevant academic research and scientific papers
General entry to asymmetric one-pot [ N + 2 + n ] cyclization for the synthesis of three- to seven-membered azacycloalkanes
Harada, Shingo,Sakai, Takeo,Takasu, Kiyosei,Yamada, Ken-Ichi,Yamamoto, Yasutomo,Tomioka, Kiyoshi
, p. 7212 - 7222 (2012/11/07)
Enantio- and diastereoselective one-pot synthesis of three- to seven-membered cis-azaheterocycles was achieved using a triggered asymmetric conjugate addition reaction of lithium amide with an enoate, followed by alkylation of the resulting lithium enolat
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
supporting information; experimental part, 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.
