TY - JOUR
T1 - Solid-phase pyrrolidine synthesis via 1,3-dipolar cycloaddition of azomethine ylides generated by the decarboxylative route
AU - Bar-Nir, Batia Ben Aroya
AU - Portnoy, Moshe
PY - 2006/2/1
Y1 - 2006/2/1
N2 - Although solid-phase pyrrolidine synthesis via dipolar cycloaddition of ester-stabilized azomethine ylides has been demonstrated on several occasions, this reaction with nonstabilized azomethine ylides, generated on solid support by a decarboxylative pathway, has never been reported. Herein we present the first solid-phase synthesis of pyrrolidines via this route and demonstrate that the reacting azomethine ylide can be generated both from a resin-bound aldehyde or amino acid. Using cyclic and acyclic dipolarophiles, bi- and monocyclic resin-bound pyrrolidines were obtained. The modest to high degree of regio- and diastereoselectivity observed in the reaction can be tuned by the substituents of the partners of this three-component process.
AB - Although solid-phase pyrrolidine synthesis via dipolar cycloaddition of ester-stabilized azomethine ylides has been demonstrated on several occasions, this reaction with nonstabilized azomethine ylides, generated on solid support by a decarboxylative pathway, has never been reported. Herein we present the first solid-phase synthesis of pyrrolidines via this route and demonstrate that the reacting azomethine ylide can be generated both from a resin-bound aldehyde or amino acid. Using cyclic and acyclic dipolarophiles, bi- and monocyclic resin-bound pyrrolidines were obtained. The modest to high degree of regio- and diastereoselectivity observed in the reaction can be tuned by the substituents of the partners of this three-component process.
UR - http://www.scopus.com/inward/record.url?scp=33646869249&partnerID=8YFLogxK
U2 - 10.3987/COM-05-S(T)47
DO - 10.3987/COM-05-S(T)47
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AN - SCOPUS:33646869249
SN - 0385-5414
VL - 67
SP - 511
EP - 518
JO - Heterocycles
JF - Heterocycles
IS - 2
ER -