NMR determination of the absolute configuration of cyclic chiral alkenes

By the use of a new axially chiral reagent, 2′-methoxy-1,1′-binaphthalene-2-carbohydroximoyl chloride (MBCC), chiral cyclic alkenes were stereoselectively derivatized into 4,5-dihydroisoxazoles. NOEs were observed between the protons of the reagent moiety and those of the alkene moiety in cycloadduc...

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Bibliographic Details
Published inTetrahedron letters Vol. 40; no. 2; pp. 325 - 328
Main Authors Fukui, Hiroki, Fukushi, Yukiharu, Tahara, Satoshi
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 01.01.1999
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
SECONDARY ALCOHOLS
REAGENTS
SPECTROSCOPY
ESTERS
ESTABLISHMENT
MTPA
NUCLEOPHILIC AROMATIC-SUBSTITUTION
O-METHYLMANDELATE
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Summary:By the use of a new axially chiral reagent, 2′-methoxy-1,1′-binaphthalene-2-carbohydroximoyl chloride (MBCC), chiral cyclic alkenes were stereoselectively derivatized into 4,5-dihydroisoxazoles. NOEs were observed between the protons of the reagent moiety and those of the alkene moiety in cycloadducts. The absolute configuration of the original alkenes was unambiguously determined by the NOE correlation. By the use of a new axially chiral reagent, (MBCC, 1), the absolute configuration of the orginal cyclic alkenes was unambiguously determined by the NOE correlation. [Display omitted]
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(98)02342-9