Synthesis of N-heterocyclic diols by diastereoselective pinacol coupling reactions

被引:9
作者
Handa, S [1 ]
Kachala, MS [1 ]
Lowe, SR [1 ]
机构
[1] Univ Leicester, Dept Chem, Leicester LE1 7RH, Leics, England
关键词
pinacol couplings; N-heterocycles; diols;
D O I
10.1016/j.tetlet.2003.10.191
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A series of 5-8 membered N-heterocyclic diols have been prepared from acyclic dicarbonyls via diastereoselective pinacol reactions whereby cis- or trans-diol stereoselectivity is controlled by the choice of low-valent metal reagent used. (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码:253 / 256
页数:4
相关论文
共 19 条
[1]  
Carpintero M, 2000, EUR J ORG CHEM, V2000, P1285, DOI 10.1002/1099-0690(200004)2000:7<1285::AID-EJOC1285>3.0.CO
[2]  
2-Z
[3]   Reductions, reductive alkylations, and intramolecular cyclizations of acyl silanes with samarium diiodide or tributyltin hydride [J].
Chuang, TH ;
Fang, JM ;
Jiaang, WT ;
Tsai, YM .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (05) :1794-1805
[4]  
de Gracia IS, 1998, J ORG CHEM, V63, P5883
[5]   Bu3SnH-mediated pinacol coupling of 1,5- and 1,6-dicarbonyl compounds:: Synthetic and mechanistic studies [J].
Hays, DS ;
Fu, GC .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (18) :6375-6381
[6]   Synthesis of 1,4-diaminocyclitols from L-serine methyl ester [J].
Kang, M ;
Park, J ;
Konradi, AW ;
Pedersen, SF .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (16) :5528-5531
[7]  
Kiguchi T, 1999, HETEROCYCLES, V51, P2711
[8]   Total synthesis of (-)-balanol [J].
Miyabe, H ;
Torieda, M ;
Inoue, K ;
Tajiri, K ;
Kiguchi, T ;
Naito, T .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (13) :4397-4407
[9]   Samarium diiodide-induced radical cyclization of oxime ether connected with formyl group: Synthesis of 4-pyrimidinyl- and 4-purinylpyrrolidin-3-ol nucleoside analogues [J].
Miyabe, H ;
Kanehira, S ;
Kume, K ;
Kandori, H ;
Naito, T .
TETRAHEDRON, 1998, 54 (22) :5883-5892
[10]   SEQUENTIAL RADICAL CYCLIZATION INTERMOLECULAR CARBONYL ADDITION-REACTIONS INITIATED BY SAMARIUM(II) IODIDE [J].
MOLANDER, GA ;
KENNY, C .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (04) :1439-1445