25756-02-9Relevant articles and documents
Highly Diastereoselective Reactions of Isoxazolidine-4,5-diols with Grignard Reagents: A New Approach to anti, syn -γ-Amino-α,β-diols
?urina, Luká?,Malatinsky, Tomá?,Moncol, Ján,Záborsky, Ondrej,Fischer, Róbert
, p. 688 - 698 (2020/11/13)
An investigation of the reaction of 3,4- trans -isoxazolidine-4,5-diols with Grignard reagents is described for the first time. Their resemblance to five-membered cyclic hemiacetals allows them to react as α-hydroxy-β-(hydroxyamino)aldehydes in a highly stereoselective manner, providing anti, syn -γ-(hydroxyamino)-α,β-diols in moderate yields and with good to excellent syn -diastereoselectivities, which can be improved by the addition of anhydrous cerium chloride. The obtained (hydroxyamino-)diols serve as suitable precursors of anti, syn -γ-amino-α,β-diols that represent valuable scaffolds for the synthesis of various biologically active compounds.
Efficient and regioselective synthesis of 5-hydroxy-2-isoxazolines: Versatile synthons for isoxazoles, β-lactams, and γ-amino alcohols
Tang, Shibing,He, Jinmei,Sun, Yongquan,He, Liuer,She, Xuegong
supporting information; scheme or table, p. 1961 - 1966 (2010/06/20)
"Chemical Equation Presented" An efficient and highly regioselective protocol was developed for the preparation of 5-hydroxy2-isoxazolines, which have been proved to be versatile synthons for isoxazles, β-hydroxy oximes, and γ-amino alcohols. β-Lactams, commonly embedded in the skeletons of bioactive natural products, were also synthesized in two steps from β-hydroxy oximes, providing a new strategy for the synthesis of this kind of compounds.
Generation of chromioenamines by reduction of O-acetyloximes with chromium(II) and their application
Takai,Katsura,Kunisada
, p. 1724 - 1725 (2007/10/03)
Chromioenamines can be generated by treatment of O-acetyloximes with chromium(II) via two steps of one-electron reduction and successive isomerization, and the species react with aldehydes to give γ-amino alcohols after reduction with LiA1H4.
