300348-88-3Relevant articles and documents
Bicarbonate Salts as Cost-Effective Bases for the Synthesis of Ketenes and Their Synthetic Equivalents Applied to the Asymmetric Synthesis of β-Lactams
Shah, Meha H.,France, Stefan,Lectka, Thomas
, p. 1937 - 1939 (2003)
We report the use of bicarbonate salts as viable alternatives to more expensive bases for the in situ generation of ketenes and their synthetic equivalents. We have successfully applied this to the catalytic, asymmetric synthesis of β-lactams.
Column asymmetric catalysis for beta-lactam synthesis.
Hafez,Taggi,Wack,Drury 3rd.,Lectka
, p. 3963 - 3965 (2000)
[structure] A catalytic asymmetric reaction process was designed involving the use of solid-phase reagents and catalysts that constitute the packing of a series of "reaction columns". This process was applied to the catalytic asymmetric synthesis of beta-
Molecular mechanics calculations as predictors of enantioselectivity for chiral nucleophile catalyzed reactions
Taggi, Andrew E.,Hafez, Ahmed M.,Dudding, Travis,Lectka, Thomas
, p. 8351 - 8356 (2002)
We present molecular mechanics (MM) calculations as models of activated complexes for the β-lactam forming [2+2] cycloaddition between imino ester 4 and the zwitterionic intermediates derived from ketenes and various chiral nucleophilic catalysts. Our met
Bifunctional Lewis acid-nucleophile-based asymmetric catalysis: Mechanistic evidence for imine activation working in tandem with chiral enolate formation in the synthesis of β-lactams
France, Stefan,Shah, Meha H.,Weatherwax, Anthony,Wack, Harald,Roth, Justine P.,Lectka, Thomas
, p. 1206 - 1215 (2007/10/03)
We report a mechanistically based study of bifunctional catalyst systems in which chiral nucleophiles work in conjunction with Lewis acids to produce β-lactams in high chemical yield, diastereoselectivity, and enantioselectivity. Chiral cinchona alkaloid