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Asymmetric, anti-Selective Scandium-Catalyzed Sakurai Additions to Glyoxyamide. Applications to the Syntheses of N-Boc d-Alloisoleucine and d-Isoleucine

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journal contribution
posted on 11.05.2006, 00:00 by David A. Evans, Yimon Aye, Jimmy Wu
An enantio- and diastereoselective Sakurai−Hosomi reaction, catalyzed by chiral scandium pyridyl-bis(oxazoline) (pybox) complexes, has been developed. Both alkyl- and aryl-substituted allylsilanes are effective coupling partners with N-phenylglyoxamide. Applications of this reaction to the asymmetric syntheses of N-Boc d-alloisoleucine and d-isoleucine are described.