A total stereospecific route to α-alkylidene-γ-lactams

Beji, Feten; Lebreton, Jacques; Villiéras, J.; Amri, Hassen

doi:10.1016/s0040-4020(01)01018-3

Cited by 37 publications

(11 citation statements)

References 24 publications

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“…It should be noted that the synthesis of allyl bromide 4 was always accompanied by the formation of its regioisomer 5, which was easily separable from the desired product 4 by silica gel column chromatography (Scheme 3). In order to establish a chemical library reserved for the various functionalized allylamines published during the last decade by our research group 30 and their use as basic skeletons of many biologically important substances [31][32][33][34][35][36][37] and numerous natural products [38][39][40][41][42][43][44][45][46][47] , we focused our attention on the synthesis of a new family of allylamines 6. The best reaction conditions were obtained following the reaction of the electrophilic allyl bromide (E)-4 with excess of monoalkylamines (2 equiv.)…”

Section: Resultsmentioning

confidence: 99%

Efficient synthesis of allylamines from a novel (E)-2,3-difunctionalized allyl bromide

Ameur¹,

Arfaoui²

2014

Arkivoc

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We report a new procedure for highly stereoselective synthesis of difunctionalized allyl and vinyl bromides E-4 and E-5 via a tandem reaction of bromination-dehydrobromination of tetraethyl prop-2-ene-1,2-diyldiphosphonate in the presence of DBU in acetonitrile at room temperature. The coupling reaction of allyl bromide E-4 with various primary amines in methanol at 0 °C, followed by S N 2' reaction, provides a new family of tetraethyl 1-(alkylamino)prop-2-ene-1,2-diyldiphosphonates 6 in high yields.

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Section: Resultsmentioning

confidence: 99%

Efficient synthesis of allylamines from a novel (E)-2,3-difunctionalized allyl bromide

Ameur¹,

Arfaoui²

2014

Arkivoc

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“…[56] S N 2Ј alkylation of various nitroalkanes with 218 and subsequent elimination of nitrous acid afforded the E-configured dienes 220 in a highly stereoselective manner. Aza-Michael additions of primary amines to the dienes 220 followed by spontaneous cyclization of compounds 221 led to the target products 222.…”

Section: Miscellaneous Methods For the Synthesis Of α-Alkylidene Lactmentioning

confidence: 99%

Recent Advances in the Synthesis of α‐Alkylidene‐Substituted δ‐Lactones, γ‐Lactams and δ‐Lactams

2011

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α-Alkylidene-substituted δ-lactones and corresponding γ-and δ-lactams constitute important classes of natural compounds that display diverse biological activities. This review gives a brief description of the occurrence and biological activities of the title compounds and then summarizes the methods available for their preparation. Attention is given mainly to the synthetic approaches developed during the last decade, including those from our own research group. The latest developments in the synthesis of nonracemic α-alkylidene-substituted δ-lactones, γ-lactams and δ-lactams are also discussed.

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“…Conjugate addition of nitroalkane to functional allyl acetates has been the subject of intensive work by our group [43][44][45][46][47] . Based on the previous results achieved by our group and others 48 , we further investigated the reactivity of allyl acetates 2b with nitronate anion generated from primary and secondary nitroalkanes toward the formation of highly substituted ethyl 1-alkylidene-1H-indene-2-carboxylates 4.…”

Section: Scheme 2 Synthesis Of Ethyl-1h-indene-2-carboxylatesmentioning

confidence: 99%