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The stereoselective conversion of 2-alkenyl alcohols to (R)- or (S)-alkane-1,2-diols using D-glucose as a chiral auxiliary

✍ Scribed by Gang Huang; Rawle I. Hollingsworth

Publisher: Elsevier Science
Year: 1999
Tongue: French
Weight: 254 KB
Volume: 40
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(98)02472-1

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✦ Synopsis

The stereoselective addition of the 2-hydroxyl group of glucose to the mercurated vinyl group of 2-alkenyl glycosides followed by hydride reduction and removal of the saccharide fragment was used to prepare enantiomerically pure 1,2-dihydroxy alkanes. Diols of (R) or (S) configuration can be synthesized from (ot)-glyeosides or the (13) form respectively. Demercuration with chloride ion led to the insertion of a halo group adjacent to the new ehiral center thus allowing for the possibility offurther funetionalization.

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