Intramolecular 4+3 cycloadditions. A theoretical analysis of simple diastereoselectivity in reactions of alkoxyallylic cations and furans

被引:18
作者
Harmata, M
Schreiner, PR
机构
[1] Univ Gottingen, Inst Organ Chem, D-37077 Gottingen, Germany
[2] Univ Georgia, Dept Chem, Athens, GA 30602 USA
关键词
D O I
10.1021/ol016611t
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] A computational examination (B3LYP/6-31+G*//HF/6-31+G* + ZPVE) of an intramolecular 4 + 3 cycloaddition reaction suggests a stepwise process and the likelihood of reversibility in at least one of the pathways examined.
引用
收藏
页码:3663 / 3665
页数:3
相关论文
共 18 条
[1]  
[Anonymous], 1997, Advances in Cycloaddition
[2]   DENSITY-FUNCTIONAL THERMOCHEMISTRY .3. THE ROLE OF EXACT EXCHANGE [J].
BECKE, AD .
JOURNAL OF CHEMICAL PHYSICS, 1993, 98 (07) :5648-5652
[3]  
Cha JK, 1998, CURR ORG CHEM, V2, P217
[4]  
Cramer CJ, 2000, J PHYS ORG CHEM, V13, P176, DOI 10.1002/(SICI)1099-1395(200003)13:3<176::AID-POC232>3.0.CO
[5]  
2-V
[6]   Intramolecular 4+3 cycloadditions. Theoretical and experimental evaluation of endo/exo preferences of a cyclopentenyl cation [J].
Cramer, CJ ;
Harmata, M ;
Rashatasakhon, P .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (16) :5641-5644
[7]   Quantum chemical characterization of cycloaddition reactions between the hydroxyallyl cation and dienes of varying nucleophilicity [J].
Cramer, CJ ;
Barrows, SE .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (16) :5523-5532
[8]  
FRISCH MJ, 1999, GAUSSIAN 98
[9]  
Harmata M, 1997, RRD ORG CHEM, V1, P523
[10]   INTRAMOLECULAR [4+3]-CYCLOADDITIONS - STUDIES OF RELATIVE ASYMMETRIC INDUCTION [J].
HARMATA, M ;
GAMLATH, CB ;
BARNES, CL ;
JONES, DE .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (16) :5077-5092