Highly regio- and stereoselective iodocyclization of chiral 3-alkoxycarbonyl-4-propenyl-2,2-dimethy-1,3-oxazolidines:: a computational investigation

被引：18
作者：
Jordá-Gregori, JM
González-Rosende, ME
Sepúlveda-Arques, J
Galeazzi, R
Orena, M
机构：
[1] Univ Ancona, Dipartimento Sci Mat & Terra, I-60131 Ancona, Italy
[2] Univ Valencia, Fac Pharm, Dept Organ Chem, E-46100 Burjassot, Spain
来源：
TETRAHEDRON-ASYMMETRY | 1999年 / 10卷 / 06期
关键词：
D O I：
10.1016/S0957-4166(99)00084-1
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
The iodocyclization of allylic carbamates 3a and 3b proceeded with high regio- and stereoselection to give 2-oxobicyclo[4.3.0]nonane 5a as the major product. Both the regio- and diastereoselection of the reaction were investigated with the help of molecular mechanics and quantomechanical calculations. The energetic difference between the competing transition states TS-5a and TS-Sb is in good agreement with the experimental results and from the calculated transition structures it appears that steric factors direct the discrimination. (C) 1999 Elsevier Science Ltd. All rights reserved.
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页码：1135 / 1143
页数：9
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