Journal ArticleDOI
Pentacovalent Phosphorus in Organic Synthesis: A New Route to Substituted Phosphonates
TLDR
The pentacovalent oxaphospholene derived from methyl vinyl ketone and trialkyl phosphite has been shown to condense with a variety of electrophiles to produce highly substituted phosphonates as discussed by the authors.Abstract:
The pentacovalent oxaphospholene derived from methyl vinyl ketone and trialkyl phosphite has been shown to condense with a variety of electrophiles to produce highly substituted phosphonates.read more
Citations
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Journal ArticleDOI
Heterophosphacyclanes in organic synthesis
TL;DR: In this paper, a systematic account of the use of mono-and di-heterophosphacyclanes, containing σ3-, σ 4- and σ 5- phosphorus atoms, for the synthesis of phosphorus-free organic substances is given.
Journal ArticleDOI
A C(sp3)-C(sp3) bond forming reductive condensation of α-keto esters and enolizable carbon pronucleophiles.
TL;DR: The preparation of densely functionalized unsymmetrical 1,4-dicarbonyl structural motifs by a phosphorus(III)-mediated reductive condensation of α-keto esters and enolizable carbon pronucleophiles is described.
Journal ArticleDOI
Synthetic Studies toward the Preparation of Phosphonate Analogs of Sphingomyelin and Ceramide 1-Phosphate Using Pentacovalent Organophospholene Methodology.
TL;DR: Model studies for the syntheses of phosphonate analogs of sphingomyelin and ceramide 1-phosphate are described and confirmation of stereochemical assignments in 11 (3:1, trans:cis) was accomplished via NOE experiments.
Journal ArticleDOI
Synthesis of a novel cyclic pentacovalent phosphoenol ether derived from a dienone. Approaches to the syntheses of phosphonate analogs of sphingomyelin, sphingosine 1-phosphate and ceramide 1-phosphate
Cynthia K. McClure,Pranab Mishra +1 more
TL;DR: The synthesis of a new pentacovalent oxaphospholene from a dienone, and its use as an enolate equivalent in the approach toward the syntheses of a phosphonate analog of sphingomyelin, sphingosine 1-phosphate and ceramide 1- phosphate is described.
Book ChapterDOI
4.12 – Functions Containing One Phosphorus and Either Another Phosphorus or As, Sb, Bi, Si, Ge, B or a Metal
TL;DR: New developments in the synthesis of organic compounds containing the PCP function are described in this article, categorized according to the coordination number of each phosphorus atom and then according to methods used.
References
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Journal ArticleDOI
Applications of oxaziridines in organic synthesis
TL;DR: In this paper, les N-aryl-and Nalkyl oxaziridines and leurs reactivites lors de reactions de transfert d'oxygene, de reactions nucleophiles and de transpositions chimiques are discussed.
Journal ArticleDOI
Asymmetric electrophilic amination - synthesis of alpha-amino and alpha-hydrazino acids with high optical purity
TL;DR: In this article, a synthese est realisee a partir de l'acetal de cetene derive du propionate de N-methylephedrine.
Journal ArticleDOI
Pentacovalent oxaphosphorane chemistry in organic synthesis: a new route to substituted phosphonates
Cynthia K. McClure,K.‐Y. Jung +1 more
Journal ArticleDOI
Pentacovalent oxaphosphorane chemistry in organic synthesis. 2. Total syntheses of (.+-.)-trans- and (.+-.)-cis-neocnidilides
Cynthia K. McClure,K.‐Y. Jung +1 more
TL;DR: Both (±)-trans-and (±-)cis-neocnidlides (1 and 2) have been synthesized via the route illustrated in Scheme III as discussed by the authors, where the condensation of the 1,2λ 5 -oxaphospholene 5b with valeraldehyde produced highly substituted phosphonates 12s and 12a, which were transformed via an intramolecular Wadsworth-Horner-Emmons olefination reaction to the title compounds