“…Reaction of nitroalkanes with dimethyl α-(bromomethyl)fumarate 263 follows the usual addition−elimination mechanism giving diene derivative 264 (Scheme ). , Aliphatic amines react with diene 264 by means of a conjugate addition−cyclization process to afford alkylidene lactams 265 . 75 …”
“…Reaction of nitroalkanes with dimethyl α-(bromomethyl)fumarate 263 follows the usual addition−elimination mechanism giving diene derivative 264 (Scheme ). , Aliphatic amines react with diene 264 by means of a conjugate addition−cyclization process to afford alkylidene lactams 265 . 75 …”
“…In previous work, we described a simple and convenient synthesis of b-functionalized a-(bromomethyl) acrylic acid ester 1a and demonstrated that it can be utilized to prepare some a-(gem-difunctional methyl) acrylic acid esters. 28,29 It seemed plausible to elaborate a new electrophilic difunctional allylic bromide such as 5, readily obtained using the known tandem It is important to indicate that the regioisomer 4 could also be effectively converted into allyl bromide 5 through a simple transformation of the conjugated cyanoester 4 in the presence of Nbromosuccinimide (NBS) 31 Allylamines are interesting synthetic targets because of their key function as intermediates in several synthetic fields, as well as their physiological properties, 32 biological activities 33,34 and their presence in several natural products. 35,36 Two main pathways can be considered for the reaction of allyl bromide 5 with primary amines in methanol.…”
“…25 Total regioselectivity has been rarely reported and concerns particular reactants and/or specific reaction conditions. Such a unique observation was described by Béji et al 26 Dimethyl bromomethylfumarate reacted stereoselectively with the diethyl phosphite anion at low temperature to produce exclusively a secondary phosphonate, the S N 2' product. By comparison, the substitution of the same allyl system with triethyl phosphite produced a mixture of primary and secondary phosphonates.…”
Section: Reactivity Of the Morita-baylis-hillman Bromides With Phosphmentioning
Morita-Baylis-Hillman adducts (e.g., activated allyl acetates or bromides) are an unprecedented trifunctional synthetic platform for diverse types of nucleophilic displacements, additions and rearrangements. These reactions can proceed in an inter-or intramolecular manner, and with stereoselective induction. Accordingly, they contribute, as the key steps, to numerous synthetic pathways, including the total syntheses of natural products of various classes and to novel strategies leading to medicinally relevant compounds and commercialized drugs. The synthetic feasibility of the Morita-Baylis-Hillman adducts in organophosphorus chemistry has been explored to a relatively low extent. In this review, we summarize the current state of the art on the formation of the C-P bond by means of the title reactions. The scope of the processes, the stereochemistry of the products and their further synthetic relevance to obtain multifunctional compounds, including those that are biologically active, are summarized.
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