Addition of dianions of 3-hydroxybutyrates to benzylideneaniline results in direct formation of trans S\*-3-(1-hydroxyethyl)-1,4-diphenyl-2-azetidinone with 95% diastereoselectivity. Inversion of theconfiguration at C, gives the desired trans R\*-2-azetidinone in high yield. --
3-(1′-hydroxyethyl)-2-azetidinones from 3-hydroxybutyrates and n-arylaldimines
✍ Scribed by Gunda I. Georg; Harpal S. Gill; Cathy Gerhardt
- Publisher
- Elsevier Science
- Year
- 1985
- Tongue
- French
- Weight
- 213 KB
- Volume
- 26
- Category
- Article
- ISSN
- 0040-4039
No coin nor oath required. For personal study only.
✦ Synopsis
Dianion imine addition, cyclisation reaction between ethyl-3-hydroxyhutyrate and aldimines generates +lactams
with the hydroxyethyl sidechain of thienamycin and related B-lactam antibiotics in place.
The effects of the N-arylaldimine and the reaction conditions on the sterochemistry of the resulting products are examined.
📜 SIMILAR VOLUMES
The enolate-imine condensation of the lithio dianion 8 of ethyl 3-hydroxybutyrate 7 with Nanisylcinnamylideneimine was studied in the presence of a variety of metal salts and organometallic reagents. Addition of terr-butyl magnesium chloride to the reaction mixture produced the reZ(l'R,3R,4S)-3-(l'-
The title compound, [Fe(C 5 H 5 )(C 11 H 13 N 2 O)]Á[Fe(C 5 H 5 )-(C 11 H 13 N 2 O)]Cl, cocrystallizes as (1-2-hydroxyethyl-5methylpyrazol-3-yl)ferrocenium chloride-(1-2-hydroxyethyl-5-methylpyrazol-3-yl)ferrocene (1/1). Two independent pyrazolylferrocenes in the asymmetric unit, with similar geomet