## 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 res
Stereoselective synthesis of 3-(1-Hydroxyethyl)-2-azetidinonesfrom 3-hydroxybutyrates
✍ Scribed by Gunda I. Georg
- Publisher
- Elsevier Science
- Year
- 1984
- Tongue
- French
- Weight
- 206 KB
- Volume
- 25
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
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. --
📜 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'-
Michael-addition of nitromethane anion to 5-ylidene-1,3-dioxane-4-ones 2 gives high yields of 5-(13-nitroalkyl)-l,3-dioxane-4-ones 3 and 4 with a preponderance of 3 (reattack). Hydrogenation of the products in the presence of Raney-Ni affords optically active 4-substituted cis-3-(o~-hydroxyethyl)-py
## Abstract 1‐(4‐Chlorobenzyl)‐3‐methyl‐3‐(2‐hydroxyethyl)‐thiourea labelled with ^14^C at its urea group was synthesised starting from potassium cyanide‐^14^C, via potassium thiocyanate‐^14^C, 4‐chlorobenzyl‐thiocyanate‐^14^C and 4‐chlorobenzyl‐isothiocyanate‐^14^C. The conditions of the isomerisa