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Six‐Membered Ring Formation from Lewis Acid Promoted Reactions of 2‐Substituted 2‐Alkenyl Amides and Esters of Ethenetricarboxylate
Author(s) -
Yamazaki Shoko,
Ueda Kohta,
Fukushima Yugo,
Ogawa Akiya,
Kakiuchi Kiyomi
Publication year - 2014
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.201402637
Subject(s) - chemistry , lewis acids and bases , ring (chemistry) , dihydropyran , propenyl , medicinal chemistry , stereochemistry , organic chemistry , catalysis
The Lewis acid promoted reactions of 2‐substituted 2‐propenyl amides and the 2‐methylbuta‐2,3‐dienyl ester of ethenetricarboxylate have been examined. The reactions of 2‐substituted 2‐propenyl amides with AlCl 3 gave 2‐oxo‐5,6‐dehydropiperidines as the major products. The reaction of 2‐methylbuta‐2,3‐dienyl ester with Lewis acids such as AlCl 3 and SnCl 4 gave 2‐oxo‐3,6‐dihydropyran as the major product. The preference for six‐ over five‐membered‐ring formation was observed.