Oxidation of 3-alkylidene-β-lactams. A preparation of 3-alkenyl-3-hydroxy-β-lactams
- 1 February 1988
- journal article
- research article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 66 (2) , 304-309
- https://doi.org/10.1139/v88-053
Abstract
Hydroxylation of the enolates of several 3-alkylideneazetidin-2-ones with MoOPH leads to the formation of 3-hydroxy-3-alkenylazetidin-2-ones in fair to good yields. The products were formed with trans stereochemistry in the alkenyl moiety and a presumed trans relationship between the hydroxyl substituent and a 4-substituent. Hydrogenation leads to 3-alkyl-3-hydroxy-azetidin-2-ones. The prerequisite 3-alkylideneazetidin-2-ones were formed from 3-trimethylsilylazetidin-2-ones and aldehydes via a Peterson olefin synthesis.This publication has 1 reference indexed in Scilit:
- Thienamycin total synthesis. 1. Synthesis of azetidinone precursors of (.+-.)-thienamycin and its stereoisomersThe Journal of Organic Chemistry, 1980