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Diastereocontrol via lewis acid-promoted ene reaction with glyoxylates and its application to stereocontrolled synthesis of a 22R-hydroxy-23-carboxylate steroid side chain

✍ Scribed by Kōichi Mikami; Teck-Peng Loh; Takeshi Nakai

Publisher: Elsevier Science
Year: 1988
Tongue: French
Weight: 213 KB
Volume: 29
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)82332-1

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✦ Synopsis

Taking the judicious choice of the Lewis acid employed, the glyoxylate ene reactions are shown to proceed with a high level of either erythro or threo diastereoselection. The utility of the ene methodology is demonstrated through the stereocontrolled synthesis of a 22F&hydroxy-23-carboxylate steroid side chain.

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