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Efficiency of Acid‐ and Mercury‐Catalyzed Cyclization Reactions in the Synthesis of Tetrahydrofurans from Allylsilyl Alcohols
Author(s) -
Pulido Francisco J.,
Barbero Asunción,
Val Patricia,
Diez Alberto,
GonzálezOrtega Alfonso
Publication year - 2012
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201200666
Subject(s) - chemistry , stereoselectivity , mercury (programming language) , catalysis , alcohol , organic chemistry , combinatorial chemistry , computer science , programming language
The scope of the acid‐catalyzed and mercury‐catalyzed cyclization reactions of allylsilyl alcohols is described. This methodology has been found to be an efficient approach to the synthesis of highly substituted tetrahydrofurans. The stereoselectivity of the cyclization is dependent both on the substitution of the starting alcohol and on the catalyst. A plausible mechanism has been proposed that is consistent with the results.