2015
DOI: 10.1016/j.tet.2015.10.064
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Regio and diastereoselective multicomponent 1,3-dipolar cycloadditions between prolinate hydrochlorides, aldehydes and dipolarophiles for the direct synthesis of pyrrolizidines

Abstract: Please cite this article as: Mancebo-Aracil J, Nájera C, Castelló LM, Sansano JM, Larrañaga O, de Cózar A, Cossío FP, Regio and diastereoselective multicomponent 1,3-dipolar cycloadditions between prolinate hydrochlorides, aldehydes and dipolarophiles for the direct synthesis of pyrrolizidines, Tetrahedron (2015),

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Cited by 16 publications
(12 citation statements)
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“…We next transferred our attention to evaluate the three-component one-pot 1,3-dipolar cycloaddition of the in situ generated α-iminoesters from tert-butyl glycinate and different aromatic aldehydes under the action of N,N'-Diisopropylcarbodiimide (DIC) serving as a dehydrator with α-methylene-γ-butyrolactone 3 [29,30]. As shown in Scheme 3, arene-substituents with different electronic properties and steric hindrance were well tolerated and the desired endo-6a-6f were obtained in one-pot process with excellent yields (92%-97%) and moderate to high enantioselectivities (66%-90% ee).…”
Section: Study On the Construction Of Spiro Pyrrolidines By The Threementioning
confidence: 99%
“…We next transferred our attention to evaluate the three-component one-pot 1,3-dipolar cycloaddition of the in situ generated α-iminoesters from tert-butyl glycinate and different aromatic aldehydes under the action of N,N'-Diisopropylcarbodiimide (DIC) serving as a dehydrator with α-methylene-γ-butyrolactone 3 [29,30]. As shown in Scheme 3, arene-substituents with different electronic properties and steric hindrance were well tolerated and the desired endo-6a-6f were obtained in one-pot process with excellent yields (92%-97%) and moderate to high enantioselectivities (66%-90% ee).…”
Section: Study On the Construction Of Spiro Pyrrolidines By The Threementioning
confidence: 99%
“…However, working in the presence, or in the absence of AgOAc, and N-methylmaleimide as dipolarophile, a 3:1 mixture of diastereomeric adducts 77 and 78 were obtained [54] (Fig. 6).…”
Section: Multicomponent Synthesis Of Pyrrolizidines By 13-dcmentioning
confidence: 99%
“…The reaction proceeded with both high regio-and diastereoselectivity to yield heterocycles in the presence or in the absence of AgOAc as catalyst depending on the aldehyde employed (Scheme 82). 123 This cascade allowed access to diverse molecular complexity, multiplication of stereocenters, and access to potential bioactive pyrrolizidine alkaloids.…”
Section: Scheme 81 Synthesis Of Functionalized Spiropyrrolizidines Anmentioning
confidence: 99%