60204-66-2Relevant academic research and scientific papers
Pd-catalyzed intramolecular aminohydroxylation of alkenes with hydrogen peroxide as oxidant and water as nucleophile
Zhu, Haitao,Chen, Pinhong,Liu, Guosheng
, p. 1766 - 1769 (2014/03/21)
A palladium-catalyzed intramolecular aminohydroxylation of alkenes was developed, in which H2O2 was applied as the sole oxidant. A variety of related alkyl alcohols could be successfully obtained with good yields and excellent diastereoselectivities, which directly derived from oxidation cleavage of alkyl C-Pd bond by H2O2. Facile transformation of these products provided a powerful tool toward the synthesis of 2-amino-1,3-diols and 3-ol amino acids. Preliminary mechanistic studies revealed that major nucleophilic attack of water (SN2 type) at high-valent Pd center contributes to the final C-O(H) bond formation.
Directed Openings of 2,3-Epoxy Alcohols via Reactions with Isocyanates: Synthesis of (+)-erythro-Dihydrosphingosine
Roush, William R.,Adam, Michael A.
, p. 3752 - 3757 (2007/10/02)
Two methods for the synthesis of 2-(N-alkylamino) 1,3-diols from 2,3-epoxy alcohols are described.In one procedure (method A) an epoxyurethane (5, 8, 11, 14, 16) prepared from the corresponding epoxy alcohol by standard procedures is cyclized to a 2-oxazolidinone derivative (6, 9, 12, 15, 17) in 81-90percent yield by treatment with NaH in THF or NaOMe in MeOH.The second procedure (method B) involves treatment of the epoxy alcohol (4, 7, 10, 13, 24) with benzyl isocyanate, an NH3 synthetic equivalent, and NaH in THF at reflux.Hydrolysis of the crude isoxazolidinones by exposure to LiOH in EtOH at reflux smoothly affords 2-(N-benzylamino) 1,3-diols (22, 23, 30, 31) in 68-72percent overall yield.These procedures are highly regioselective; products resulting from intramolecular addition of the urethane nitrogen atom to the epoxide β-position were not detected.This methodology was applied to a short, highly stereoselective synthesis of (+)-erythro-dihydrosphingosine (26) from palmitic aldehyde ( 47-54percent overall yield).
