| Title | Regioselective Ring Expansion of 2,4-Diiminoazetidines via Cleavage of C-N and C(sp(3))-H Bonds: Efficient Construction of 2,3-Dihydropyrimidinesulfonamides |
| Authors | Wang, Yang Chi, Yue Zhang, Wen-Xiong Xi, Zhenfeng |
| Affiliation | Peking Univ, Coll Chemisstry, Beijing Natl Lab Mol Sci, Beijing 100871, Peoples R China. Peking Univ, Coll Chemisstry, Minist Educ, Key Lab Bioorgan Chem & Mol Engn, Beijing 100871, Peoples R China. Nankai Univ, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China. |
| Keywords | EARTH-METAL COMPLEXES CATALYTIC ADDITION BETA-LACTAMS ALPHA,BETA-UNSATURATED AMIDINES STEREOSELECTIVE-SYNTHESIS MULTICOMPONENT REACTIONS SUCCINIMIDE DERIVATIVES SUBSTITUTED GUANIDINES TERMINAL ALKYNES BUILDING-BLOCKS |
| Issue Date | 2012 |
| Publisher | journal of the american chemical society |
| Citation | JOURNAL OF THE AMERICAN CHEMICAL SOCIETY.2012,134,(6),2926-2929. |
| Abstract | A highly regioselective base-mediated ring expansion of 2,4-diiminoazetidines via cleavage of C-N and C(sp(3))-H bonds is achieved for the first time to afford efficiently 2,3-dihydropyrimidinesulfonamides. The mechanism of the ring expansion via tandem 4 pi electrocyclic ring-opening/1,5-H shift/6 pi electrocydic ring-closing is well confirmed by the trapping experiments of two key intermediates and deuterium labeling studies. |
| URI | http://hdl.handle.net/20.500.11897/191669 |
| ISSN | 0002-7863 |
| DOI | 10.1021/ja211486f |
| Indexed | SCI(E) EI PubMed |
| Appears in Collections: | å å¦ä¸ å å å·¥ç¨ å¦é ¢ 生物有机与分子工程教育部重点实验室 |
