13286-60-7Relevant 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 (2021)
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.
Stereoselective Preparation of Acyclic syn-β-Amino Alcohols from β-Hydroxy Ketones via the Corresponding O-Benzyl Oximes
Narasaka, Koichi,Ukaji, Yutaka,Yamazaki, Shigeru
, p. 525 - 534 (2007/10/02)
Reduction of β-hydroxy ketone O-benzyl oximes with lithium aluminum hydride in the presence of sodium or potassium methoxide afforded the corresponding syn-β-amino alcohols in highly stereoselective manner.A lythraceae alkaloid, lasubine II, was synthesiz