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An Asymmetric Domino Three-Component Synthesis of β-Lactams (1998)

Palomo, Claudio ; Aizpurua, Jesús M. ; Gracenea, José Javier ; [et al.]

Weinheim : Wiley-Blackwell

Liebigs Annalen 1998 (1998), S. 2201-2207

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ISSN: 1434-193X

Keywords: Antibiotics ; Asymmetric synthesis ; β-Lactams ; Michael additions ; Multicomponent reactions ; Chemistry ; General Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: Lithium dialkylcuprates react either in a sequential one-pot or in a domino “three-component” fashion with chiral Michael acceptors, like Oppolzer's N-enoyl-2,10-camphorsultams 7 and 11 or ‘Evans’ N-enoyl-4-phenyl-1,3-oxazolidin-2-ones 8 and 13, and N-(methoxycarbonylmethylidene)(4-methoxyphenyl)amine 9 to afford the corresponding cis-3-alkyl-4-methoxycarbonyl-1-(4-methoxyphenyl)azetidin-2-ones 10, 14-15 in overall yields of 40-67% and enantiomeric excesses of 91-99%.

Type of Medium: Electronic Resource

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