FeCl3-Promoted One-Step Synthesis of Spiro[4.5]decane Derivatives

被引:4
作者
Zheng, Deping [1 ]
Ma, Zuodong [1 ]
Gong, Wanchun [1 ]
Xie, Zhixiang [1 ]
Li, Ying [1 ]
机构
[1] Lanzhou Univ, Coll Chem & Chem Engn, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China
基金
中国国家自然科学基金;
关键词
spiro[4.5]decane; FeCl3; Prins cyclization; alpha-hydroxy alkynyl acetals; diastereoselectivity; PRINS-PINACOL SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; SILICA-GEL; CYCLIZATION; RING; CHLORIDE; ANNULATIONS; REAGENT; ACETALS; ETHER;
D O I
10.1055/s-0030-1258541
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A FeCl3-promoted synthesis of spiro[4.5]decane derivatives has been developed from 2-(5,5-dimethoxypentyl)-1-substituted cyclopentanols with high diastereoselectivity. These interesting compounds are formed through a cascade process involving a FeCl3-promoted dehydration of alcohol followed by FeCl3-mediated Prins cyclization.
引用
收藏
页码:2169 / 2173
页数:5
相关论文
共 22 条
[1]   ACID-PROMOTED REACTION OF CYCLIC ALLYLIC DIOLS WITH CARBONYL-COMPOUNDS - STEREOSELECTIVE RING-ENLARGING TETRAHYDROFURAN ANNULATIONS [J].
BROWN, MJ ;
HARRISON, T ;
HERRINTON, PM ;
HOPKINS, MH ;
HUTCHINSON, KD ;
MISHRA, P ;
OVERMAN, LE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (14) :5365-5378
[2]  
Burke BJ, 2004, SYNLETT, P1387
[3]   An oxidative Prins cyclization methodology [J].
Chen, CF ;
Mariano, PS .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (10) :3252-3254
[4]   Stereoselection in the prins-pinacol synthesis of acyltetrahydrofurans [J].
Cohen, F ;
MacMillan, DWC ;
Overman, LE ;
Romero, A .
ORGANIC LETTERS, 2001, 3 (08) :1225-1228
[5]   Recent uses of iron (III) chloride in organic synthesis [J].
Díaz, DD ;
Miranda, PO ;
Padrón, JI ;
Martín, VS .
CURRENT ORGANIC CHEMISTRY, 2006, 10 (04) :457-476
[6]   ANHYDROUS FERRIC-CHLORIDE ADSORBED ON SILICA-GEL INDUCED RING ENLARGEMENT OF TERTIARY CYCLOBUTANOLS - SYNTHESIS OF ISOLAUROLENE AND DERIVATIVES, CAMPHOLENIC ETHER AND (+/-)CUPARENE [J].
FADEL, A ;
SALAUN, J .
TETRAHEDRON, 1985, 41 (02) :413-420
[7]   Stereoselective synthesis of carbocyclic ring systems by pinacol-terminated Prins cyclizations [J].
Gahman, TC ;
Overman, LE .
TETRAHEDRON, 2002, 58 (32) :6473-6483
[8]   Stereoselection in the prins-pinacol synthesis of 2,2-disubstituted 4-acyltetrahydrofurans. Enantioselective synthesis of (-)-citreoviral [J].
Hanaki, N ;
Link, JT ;
MacMillan, DWC ;
Overman, LE ;
Trankle, WG ;
Wurster, JA .
ORGANIC LETTERS, 2000, 2 (02) :223-226
[9]   STEREOCONTROLLED PREPARATION OF TETRAHYDROFURANS FROM ACID-PROMOTED REARRANGEMENTS OF ALLYLIC ACETALS [J].
HOPKINS, MH ;
OVERMAN, LE ;
RISHTON, GM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (14) :5354-5365
[10]  
Ishihara K, 2000, SYNLETT, P1245