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NMR determination of the absolute configuration of cyclic chiral alkenes

โœ Scribed by Hiroki Fukui; Yukiharu Fukushi; Satoshi Tahara

Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
217 KB
Volume
40
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

By the use of a new axially chiral reagent, 2'-methoxy-l,l'-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.

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Sutmnary: Absolute configurations of axially chiral biaryls with hydroxyl, amino, and carboxyl groups can be easily determined by pmr spectra using MTPA derivatives and shift reagents. Recently chiral biaryls have been successfully utilized in the field of asynetric synthesis\*. For example, virtual