40033-95-2Relevant academic research and scientific papers
Soluble polymer-supported synthesis of trans β-lactams with high diastereoselectivity
Jian, Shan-Zhong,Wang, Yan-Guang
, p. 866 - 867 (2004)
A general method for the liquid-phase synthesis of trans β-lactams with high diastereoselectivity is described. The mechanism can be explained by a chair-like transition state involving the imine and the (Z)-enolate.
2-Substituted 2,3-dihydro-4H-1,3-benzoxazin-4-ones: Novel auxiliaries for stereoselective synthesis of 1-β-methylcarbapenems
Kondo,Seki,Kuroda,Yamanaka,Iwasaki
, p. 2877 - 2884 (2007/10/03)
The dihydrobenzoxazone 9e, which is easily prepared from salicylamide 11 and cyclohexanone, serves as an efficient auxiliary in the synthesis of the 1-β-methylcarbapenem key intermediate 10. The stereocontrolled Reformatsky-type reactions of the acetoxyazetidinone 2 with the carboximides 6 gave the intermediates 7 with high diastereoselectivities in high chemical yields. The auxiliary 9e also acts as a good leaving guoup in the TMSCl-promoted Dieckmann-type cyclization leading to a 1-β-methylcarbapenem skeleton. By using this auxiliary, 10 was synthesized in 58% overall yield and four steps from 2.
