Diethylzinc: A chain-transfer agent in intermolecular radical additions. A parallel with triethylborane

被引:105
作者
Bertrand, MP [1 ]
Feray, L [1 ]
Nouguier, R [1 ]
Perfetti, P [1 ]
机构
[1] Univ Aix Marseille 3, Fac Sci St Jerome, UMR 6517, Lab Chim Mol Organ, F-13397 Marseille 20, France
关键词
D O I
10.1021/jo9912404
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In the presence of oxygen, diethylzinc can be used to promote radical additions to C=N bond containing radical accepters and to enones. In these reactions, it plays at the same time the role of the initiator and the role of the chain-transfer reagent. A parallel with triethylborane-mediated reactions is established. The methodology is restricted to secondary and tertiaryalkyl radicals generated from the corresponding alkyl iodides. It could not be extended either to C=C bond containing radical accepters such as methyl methacrylate and nitrocyclohexene or to diethylazodicarboxylate.
引用
收藏
页码:9189 / 9193
页数:5
相关论文
共 52 条
[1]   Asymmetric conjugate addition of diethyl zinc to enones with chiral phosphorus ligands derived from TADDOL [J].
Alexakis, A ;
Vastra, J ;
Burton, J ;
Benhaim, C ;
Mangeney, P .
TETRAHEDRON LETTERS, 1998, 39 (43) :7869-7872
[2]   Preparation and use of aziridino alcohols as promoters for the enantioselective addition of dialkylzinc reagents to N-(diphenylphosphinoyl) imines [J].
Andersson, PG ;
Guijarro, D ;
Tanner, D .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (21) :7364-7375
[3]   Stereoselective synthesis of racemic α-amino-acid derivatives with a β-lactam skeleton:: Application of the Staudinger reaction to chiral imines of methyl glyoxylate [J].
Barreau, M ;
Commercon, A ;
Mignani, S ;
Mouysset, D ;
Perfetti, P ;
Stella, L .
TETRAHEDRON, 1998, 54 (38) :11501-11516
[4]  
Bertrand MP, 1999, SYNLETT, P1148
[5]  
Bertrand MP, 1998, SYNLETT, P780
[6]   Synthesis of novel nucleic acid mimics via the stereoselective intermolecular radical coupling of 3'-iodo nucleosides and formaldoximes [J].
Bhat, B ;
Swayze, EE ;
Wheeler, P ;
Dimock, S ;
Perbost, M ;
Sanghvi, YS .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (23) :8186-8199
[9]   Photoinduced synthesis of diorganozinc and organozinc iodide reagents [J].
Charette, AB ;
Beauchemin, A ;
Marcoux, JF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (20) :5114-5115
[10]   Zinc-mediated asymmetric epoxidation of nitro alkenes with oxygen [J].
Enders, D ;
Kramps, L ;
Zhu, JQ .
TETRAHEDRON-ASYMMETRY, 1998, 9 (22) :3959-3962