Syntheses of chiral intermediates of 1-β-methylcarbapenems: (3S,4R)-3-[1(R)-tert-butyldimethylsilyloxyethyl]-4-chloroazetidin-2-one and (3S,4S)-3-[1(R)-tert-butyldimethylsilyloxyethyl]-4-[1(R)-tert-butylthiocarbonylethyl]azetidin-2-one
- 1 September 1987
- journal article
- research article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 65 (9) , 2140-2145
- https://doi.org/10.1139/v87-357
Abstract
The 4-chloroazetidinone 10, a very reactive chiral intermediate for 1-.beta.-methylcarbapenems (1b), was easily prepared and isolated as a solid crystalline compound from the corresponding sulfide 5. Another chiral intermediate (16d) bearing the 1-.beta.-methyl moiety was prepared by stereoselective aldol type condensation of either azetidinone 4 or 10 with metal enolates 14. The .beta./.alpha. ratios were 9:1, 3:1, and 2:1 respectively.This publication has 3 references indexed in Scilit:
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