436807-13-5Relevant academic research and scientific papers
Synthesis of Cyclic and Acyclic β-Amino Acids via Chelation-Controlled 1,3-Dipolar Cycloaddition
Hanselmann, Roger,Zhou, Jiacheng,Ma, Philip,Confalone, Pat N.
, p. 8739 - 8741 (2007/10/03)
Isoxazolidines have been synthesized in diastereomeric excess up to 94% via a MgBr2-induced chelation-controlled 1,3-dipolar cycloaddition reaction with N-hydroxyphenylglycinol as a chiral auxiliary. The diastereomerically pure isoxazolidines were further transformed into cyclic and acyclic β-amino acid derivatives.
A stereoselective intramolecular 1,3-dipolar nitrone cycloaddition for the synthesis of substituted chromanes
Zhao, Qian,Han, Fusen,Romero, Donna L.
, p. 3317 - 3322 (2007/10/03)
A stereoselective intramolecular 1,3-dipolar nitrone cycloaddition useful in the synthesis of chromanes is described. The reaction relies on the use of a chiral auxiliary on the nitrone partner. Key to the success of the reaction is the choice of auxiliary and the choice of Lewis acid catalyst. Utilizing an auxiliary with a pendant coordinating group, and Zn(OTf)2 as the Lewis acid, diastereoselectivities up to 22:1 could be achieved.
