SYNTHESIS OF BICYCLIC FUSED CARBOCYCLES VIA INTRAMOLECULAR DEHYDRATIVE ALKYLATION

被引:11
作者
YU, JR
CHO, HS
FALCK, JR
机构
[1] UNIV TEXAS,SW MED CTR,DEPT MOLEC GENET,DALLAS,TX 75235
[2] UNIV TEXAS,SW MED CTR,DEPT PHARMACOL,DALLAS,TX 75235
基金
美国国家卫生研究院;
关键词
D O I
10.1016/0040-4039(95)01853-A
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Intramolecular dehydrative alkylation of allylic alcohols affords fused bicyclic carbocycles. Attack at the gamma-olefinic carbon (S-N') furnishes cis-ring fusions only irrespective of precursor stereochemistry, whereas addition to the alpha-carbon results in inversion of configuration.
引用
收藏
页码:8577 / 8580
页数:4
相关论文
共 16 条
[1]   SYNTHESIS OF CYCLOALKENES BY INTRAMOLECULAR WITTIG REACTION [J].
BECKER, KB .
HELVETICA CHIMICA ACTA, 1977, 60 (01) :68-80
[2]   THE MECHANISM OF THE MITSUNOBU REACTION .3. THE USE OF TRIBUTYLPHOSPHINE [J].
CAMP, D ;
JENKINS, ID .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1992, 45 (01) :47-55
[3]  
Falck J. R., 1994, Tetrahedron Letters, V35, P5997, DOI 10.1016/0040-4039(94)88058-1
[4]  
Ho, 1988, CARBOCYCLE CONSTRUCT
[5]  
Hughes D. L., 1992, ORGANIC REACTIONS, V42, P335, DOI DOI 10.1002/0471264180.0R042.02
[7]   2-CARBON ELONGATION/ANNULATION OF ALCOHOLS TO NITRILES [J].
LAI, JY ;
YU, JR ;
HAWKINS, RD ;
FALCK, JR .
TETRAHEDRON LETTERS, 1995, 36 (32) :5691-5694
[8]  
LEE GH, 1993, TETRAHEDRON LETT, V34, P4541
[9]  
MACOR JE, 1993, HETEROCYCLES, V35, P349
[10]   THE INTRAMOLECULAR S(N') REACTION [J].
PAQUETTE, LA ;
STIRLING, CJM .
TETRAHEDRON, 1992, 48 (36) :7383-7423