chiral base mediated transformation of cyclic 1,3-diketones

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2007 Diastereoselective syntheses O 0031 Chiral Base Mediated Transformation of Cyclic 1,3-Diketones. — Treatment of cyclic 1,3-diketones (I) with a chiral lithium amide base results in formation of a non-racemic lithium monoenolate. These intermediates can be transformed directly into hydroxyketone products (II) and (IV) by reduction with DIBAL-H or addition of Grignard reagent (III), respectively. — (BUTLER, B.; SCHULTZ, T.; SIMPKINS*, N. S.; Chem. Commun. (Cambridge) 2006, 34, 3634-3636; Sch. Chem., Univ. Nottingham, Nottingham NG7 2RD, UK; Eng.) — M. Paetzel 03- 025

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Page 1: Chiral Base Mediated Transformation of Cyclic 1,3-Diketones

2007

Diastereoselective synthesesO 0031 Chiral Base Mediated Transformation of Cyclic 1,3-Diketones. — Treatment of

cyclic 1,3-diketones (I) with a chiral lithium amide base results in formation of a non-racemic lithium monoenolate. These intermediates can be transformed directly into hydroxyketone products (II) and (IV) by reduction with DIBAL-H or addition of Grignard reagent (III), respectively. — (BUTLER, B.; SCHULTZ, T.; SIMPKINS*, N. S.; Chem. Commun. (Cambridge) 2006, 34, 3634-3636; Sch. Chem., Univ. Nottingham, Nottingham NG7 2RD, UK; Eng.) — M. Paetzel

03- 025