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An Asymmetric Domino Three‐Component Synthesis of β‐Lactams
Author(s) -
Palomo Claudio,
Aizpurua Jesús M.,
Gracenea José Javier,
GarcíaGranda Santiago,
Pertierra Pilar
Publication year - 1998
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199810)1998:10<2201::aid-ejoc2201>3.0.co;2-r
Subject(s) - chemistry , domino , enantiomer , alkyl , amine gas treating , component (thermodynamics) , stereochemistry , lactam , michael reaction , medicinal chemistry , organic chemistry , catalysis , physics , thermodynamics
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%.