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Synthesis of ( E )‐3‐Alkylidenepyrrolidines by Nucleophilic Ring Closure of ( E )‐2‐Alkylidene‐1,4‐diol Derivatives
Author(s) -
Ballini Roberto,
Bosica Giovanna,
Masè Aldo,
Petrini Marino
Publication year - 2000
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 - 10.1002/1099-0690(200008)2000:16<2927::aid-ejoc2927>3.0.co;2-y
Subject(s) - chemistry , benzylamine , nucleophile , diol , ring (chemistry) , michael reaction , closure (psychology) , tandem , nucleophilic addition , organic chemistry , medicinal chemistry , allylamine , catalysis , materials science , polymer , polyelectrolyte , economics , market economy , composite material
The synthesis of N ‐protected ( E )‐3‐alkylidenepyrrolidines is reported. Nitroalkanes react with unsaturated 1,4‐diesters and 1,4‐keto esters, giving a tandem Michael addition/elimination of nitrous acid. The obtained 1,4‐dicarbonyl compounds are reduced to the corresponding diols and then converted into their mesylates. Reaction of mesylates with benzylamine or 4‐methylbenzenesulfonylamide affords the unsaturated pyrrolidines. Use of the sulfonylamide for the cyclization step has advantages over that of benzylamine, since it gives better yields of pyrrolidines, and furthermore, the benzenesulfonyl group can be efficiently removed in the presence of unsaturated bonds.