Novel regioselective synthesis of decahydrobenzocarbazoles using rhodium generated carbonyl ylides with indoles

被引：39
|
作者：
Muthusamy, S [1 ]
Gunanathan, C [1 ]
Babu, SA [1 ]
机构：
[1] Cent Salt & Marine Chem Res Inst, Silicates & Catalysis Discipline, Bhavnagar 364002, Gujarat, India
来源：
TETRAHEDRON LETTERS | 2001年 / 42卷 / 03期
关键词：
diazo compounds; indoles; carbonyl ylides; cycloaddition; rhodium acetate catalyst;
D O I：
10.1016/S0040-4039(00)01990-0
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Intermolecular cycloadditions of five-membered cyclic carbonyl ylides 3 with indole, N-methylindole and N-benzylindole afforded decahydrobenzo[c]carbazole 4a-f or decahydrocyclopenta[c]carbazole 4g-h derivatives with high regioselectivity. With N-benzoylindole and N-sulphonylindole, decahydrobenzo[c]carbazoles 4i,j and the regioisomer decahydrobenzo[a]carbazoles 5i,j are isolated. The electron withdrawing substituent reduces both regioselectivity and reactivity of the cycloadditions. This methodology generated era-bridged (unnatural) decahydrobenzocarbazole derivatives with complete control of four stereocenters. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：523 / 526
页数：4
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