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Desymmetrization of unsaturated meso-1,2-diols via an intramolecular haloetherification of ene acetals: A remarkable kinetic control

✍ Scribed by Hiromichi Fujioka; Yasushi Nagatomi; Naoyuki Kotoku; Hidetoshi Kitagawa; Yasuyuki Kita

Publisher: Elsevier Science
Year: 1998
Tongue: French
Weight: 248 KB
Volume: 39
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(98)01566-4

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✦ Synopsis

Haloetherification reaction of the chiral ene acetals derived from unsaturated meso-1,2-diols and chiral non-racemic norbornene aldehyde proceeded in an intramolecular manner with an unexpectedly high kinetic control. This method has been successfully employed for the desymmetrization of unsaturated meso-1,2-diols leading to their optically pure derivatives.

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