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Ephedrine-Derived Imidazolidin-2-ones. Broad Utility Chiral Auxiliaries in Asymmetric Synthesis (1993)

Drewes, Siegfried E. ; Malissar, Dean G. S. ; Roos, Gregory H. P.

Weinheim : Wiley-Blackwell

Berichte der deutschen chemischen Gesellschaft 126 (1993), S. 2663-2673

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ISSN: 0009-2940

Keywords: Imidazolidin-2-one, (4R,5S)-1,5-dimethyl-5-phenyl- or cyclohexyl- ; (-)-Ephedrine ; Stereoselective aldol ; alkylation, acylation ; Chemistry ; Inorganic Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: The scope of the readily available (4R,5S)-1,5-dimethyl-4-phenylimidazolidin-2-one (4) and its 4-cyclohexyl analogue 6 as practical, efficient chiral auxiliaries has been demonstrated. The enolate chemistry of their N-acyl derivatives exhibits features which recommend their use in asymmetric synthesis. The stereoselective boron-mediated aldol as well as alkylation and acylation results are presented. The steric control benefit derived by conversion of phenyl to cyclohexyl is highlighted.

Additional Material: 1 Ill.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1002/cber.19931261216

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