ChemInform Abstract: Michael Addition Reactions to 3-(4-Chloro-4,4-difluorobut-2-enoyl)oxazolidin-2-one
- Resource Type
- Authors
- Miyako Fukuda; Takashi Yamazaki; Tomoko Kawasaki-Takasuka
- Source
- ChemInform. 40
- Subject
- Addition reaction
Stereochemistry
Chemistry
Reagent
Michael reaction
General Medicine
Medicinal chemistry
- Language
- ISSN
- 1522-2667
0931-7597
1,4-Addition reactions to chlorodifluorinated Michael acceptor 1b containing a chiral oxazolidinone auxiliary were found to proceed smoothly either with alkyllithium or Grignard reagents in the presence of CuY (Y = I or CN) or ZnCl 2 . In contrast to the corresponding cuprates, R 2 Zn or R 3 ZnMgBr species (prepared from 2 or 3 equiv. of RMgX and ZnCl 2 , respectively) were quite effective in suppression of the unfavorable β-elimination mechanism leading to the terminally difluorinated byproduct 3 .