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Diastereoselectivity in the addition of organocerium reagents to 4- and 5-oxazolidonecarbaldehydes: Synthesis of syn- and anti-alcohols

✍ Scribed by Andrew G.H. Wee; Fuxing Tang

Publisher: Elsevier Science
Year: 1996
Tongue: French
Weight: 239 KB
Volume: 37
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(96)01473-6

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✦ Synopsis

Chiral non-racemic 4-and 5-oxazolidonecarbaldehydes, typified by 2 and 7, react highly diastereoselectively with organocerium reagents to give moderate to good yields of syn-and anti-alcohols, respectively. Rationalizations for the observed diastereoselectivities are presented. The synthetic potential of this method is exemplified by the synthesis of C-18-D-r/bo-phytosphingosine which was obtained as its tetraacetate.

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