Synthesis of 3-(3S-t-Butoxyl) succinimidyl-beta-lactams and the Stereoselectivity of the Reaction
Zhang Ping; Liu Na; Wang Lan-Zhi; Li Yuan
| HERO ID | 4854459 |
|---|---|
| In Press | No |
| Year | 2009 |
| Title | Synthesis of 3-(3S-t-Butoxyl) succinimidyl-beta-lactams and the Stereoselectivity of the Reaction |
| Authors | Zhang Ping; Liu Na; Wang Lan-Zhi; Li Yuan |
| Journal | Gaodeng Xuexiao Huaxue Xuebao / Chemical Journal of Chinese Universities |
| Volume | 30 |
| Issue | 1 |
| Page Numbers | 90-94 |
| Abstract | S-Malic acid is the chiral induction agent widely used in organic synthesis. In order to investigate the stereoselective synthesis of beta-lactams, eight new 3-(3S-t-butoxyl) succinimidyl-beta-lactam derivatives 2a-2h were obtained by Staudinger reaction using S-malic acid as the chiral induction agent and their structures were confirmed by (1)H NMR, IR and elemental analysis. The stereochemistry of the reaction was also investigated by the (1)H NMR, 2D NMR and X-ray diffraction analyses methods. The results indicate that the reaction of 3-(3S-t-butoxyl) succinimidyl acetyl chloride with imines(under Et(3)N) showing very good cis/trans stereoselectivity, and the trans-beta-lactam is the only product. The diastereomeric selectivity Is also good, the d. e. is between 28%-70%. |
| Wosid | WOS:000262921100021 |
| Is Certified Translation | No |
| Dupe Override | No |
| Is Public | Yes |
| Keyword | beta-Lactam; Schiff base; cis/trans stereoselectivity; Diastereomeric selectivity; Stereoselectivity |