Stereoselective Synthesis of Fluorinated Isoxazolidines and 2,3-Dihydroisoxazoles: A Cycloadditive Route to Enantiomerically Pure Amino Fluoro Alcohols

Autor:	Pierfrancesco Bravo, Cristina Pesenti, Fiorenza Viani, Walter Panzeri, Alberto Arnone, Luca Bruché
Rok vydání:	1999
Předmět:	chemistry.chemical_classification Diethyl fumarate Organic Chemistry chemistry.chemical_element Sulfoxide Asymmetric induction Cycloaddition Nitrone chemistry.chemical_compound chemistry Fluorine Organic chemistry Stereoselectivity Physical and Theoretical Chemistry Chirality (chemistry)
Zdroj:	Scopus-Elsevier
ISSN:	1099-0690 1434-193X
Popis:	3-(Fluoroalkyl)isoxazolidines 6 and -2,3-dihydroisoxazoles 8 have been obtained in enantiomerically pure form with good diastereoselectivity by 1,3-dipolar cycloaddition of diethyl fumarate and dimethylacetylene dicarboxylate, respectively, to the chiral fluorinated nitrone (R)-5. The latter has been prepared from the β-fluoromethyl-β-oxo sulfoxide (RS)-1, by a synthetic sequence where the chiral and enantiomerically pure sulfinyl function acts as a removable source of chirality. Reductive opening of isoxazolidines 6 then afforded amino fluoromethyl diols 7 in good yields.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::70f98b74c6575550108e57d545aebc74 https://doi.org/10.1002/(sici)1099-0690(199907)1999:7<1665::aid-ejoc1665>3.0.co Zobrazit plný text záznamu Plný text