Synthetic routes to β-lactams.: Some unexpected hydrogen atom transfer reactions

被引:20
作者
Boiteau, L
Boivin, J
Quiclet-Sire, B
Saunier, JB
Zard, SZ [1 ]
机构
[1] CNRS, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France
[2] Ecole Polytech, CNRS, Synth Organ Lab, F-91128 Palaiseau, France
关键词
D O I
10.1016/S0040-4020(97)10417-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Appropriately substituted xanthate derivatives of N-ethenyl acetamides undergo radical cyclisation to give beta-lactams with transfer of the xanthate group. In one case, a cascade of unexpected and unusual hydrogen transfer reactions occurred. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2087 / 2098
页数:12
相关论文
共 31 条
[1]  
BACHI MD, 1987, TETRAHEDRON LETT, V28, P2637
[2]   OLIVANIC ACID ANALOGS .1. TOTAL SYNTHESIS OF THE 7-OXO-1-AZABICYCLO[3.2.0]HEPT-2-ENE-2-CARBOXYLATE SYSTEM AND SOME RELATED BETA-LACTAMS [J].
BATESON, JH ;
BAXTER, AJG ;
ROBERTS, PM ;
SMALE, TC ;
SOUTHGATE, R .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1981, (12) :3242-3249
[3]  
Beckwith A. L. J., 1980, REARRANGEMENTS GROUN, VI, P161, DOI [10.1016/B9780-12-481301-4.50010-3, DOI 10.1016/B9780-12-481301-4.50010-3]
[4]   SYNTHESIS OF SPIRO-COMPOUNDS RELATED TO FREDERICAMYCIN-A [J].
BENNETT, SM ;
CLIVE, DLJ .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (11) :878-880
[5]  
BOSE AK, 1994, HETEROCYCLES, V39, P491
[6]  
BRUTON G, 1976, J AM CHEM SOC, V98, P6803
[7]   RADICAL CYCLIZATION REACTIONS - CYCLOPROPANE RING FORMATION BY 3-EXO-CYCLIZATION OF 5-PHENYLTHIO-3-PENTENYL RADICALS [J].
CEKOVIC, Z ;
SAICIC, R .
TETRAHEDRON LETTERS, 1990, 31 (42) :6085-6088
[8]   Chemistry of 1-alkoxy-1-glycosyl radicals: The manno- and rhamnopyranosyl series. Inversion of alpha- to beta-pyranosides and the fragmentation of anomeric radicals [J].
Crich, D ;
Sun, SX ;
Brunckova, J .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (02) :605-615
[9]   FREE-RADICAL CYCLIZATIONS LEADING TO 4-MEMBERED RINGS .1. BETA-LACTAM PRODUCTION USING TRIBUTYLTIN HYDRIDE [J].
FREMONT, SL ;
BELLETIRE, JL ;
HO, DM .
TETRAHEDRON LETTERS, 1991, 32 (21) :2335-2338
[10]   COBALT-MEDIATED REACTIONS - INTERMOLECULAR AND INTRAMOLECULAR ADDITIONS OF CARBAMOYL RADICALS TO ALKENES IN THE SYNTHESIS OF AMIDES AND LACTAMS [J].
GILL, GB ;
PATTENDEN, G ;
REYNOLDS, SJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (04) :369-378