113336-47-3Relevant academic research and scientific papers
Synthesis of new chiral hydroxy oxazolines and their use in the catalytic asymmetric phenyl transfer to aldehydes
Bolm, Carsten,Schmidt, Frank,Zani, Lorenzo
, p. 1367 - 1376 (2007/10/03)
Starting either from benzoylformic acid or ethyl oxamate and enantiopure β-amino alcohols, several chiral α-hydroxy oxazolines have been prepared by short synthetic routes. Subsequently, they have been employed in the catalytic asymmetric phenyl transfer to various aldehydes, using a mixture of triphenylborane and diethylzinc as the phenyl source. The corresponding secondary alcohols were obtained with good enantioselectivities (up to 81% ee) and up to 92% yield.
Lithium Aluminium Hydride Reduction of Chiral Benzoylformamides Derived from Chiral Amino Alcohols
Kashima, Choji,Harada, Kazuo,Omote, Yoshimori
, p. 1495 - 1500 (2007/10/02)
The reduction of benzoylformamides derived from various N- and O-substituted (S)-amino alcohols using lithium aluminium hydride was carried out.Diastereoisomeric excesses could be determined by chromatographic separation of the resulting diastereoisomeric mandelamides.In all cases, the (S,S)-diastereoisomer was obtained as the major product (1-72percent d.e.), and the degree of asymmetric induction depended largely on the N- and O-substituents of the amino alcohol moiety.A d.e. of up to 72percent was obtained for the benzoylformamide (4) derived from N-methylvalinol.
