The influence of electronic factors on palladium-mediated cycloisomerization:: a systematic investigation of competitive 5-exo-dig versus 6-endo-dig cyclizations of sugar alkynols

被引：42
作者：
Ramana, C. V. [1 ]
Mallik, Rosy [1 ]
Gonnade, Rajesh G. [1 ]
机构：
[1] Natl Chem Lab, Pune 411008, Maharashtra, India
来源：
TETRAHEDRON | 2008年 / 64卷 / 01期
关键词：
palladium; cycloisomerization; C-alkynyl furanose; spiroketal; enol ether;
D O I：
10.1016/j.tet.2007.10.072
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Pd-mediated cycloisomerization of 3-C-alkynyl-allo- and ribofuranose derivatives was investigated in detail to understand the influence of electronic factors on the regioselectivity in ring closure reaction. The reactions in general are influenced by the electronic nature of the substituent on the alkyne unit. A preference for endo-dig cyclization over exo-dig is noted, if the alkynyl substituent is not sufficiently electron withdrawing, (c) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码：219 / 233
页数：15
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