Tetraethyl vinylidenebisphosphonate: A versatile synthon for the preparation of bisphosphonates

Tetraethyl vinylidenebisphosphonate is a versatile synthetic intermediate that allows access to a variety of highly functionalized compounds bearing the bisphosphonic moiety. As an electron-deficient alkene, this compound is able to undergo conjugate addition with a variety of reagents including str...

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Autor principal:	Rodríguez, Juan Bautista
Publicado:	2014
Materias:	1 3-dipolar cycloadditions bisphosphonates Michael additions tetraethyl vinylidene bisphosphonate Amines Chemical compounds Cycloaddition Nitrogen oxides Nucleophiles Olefins Organometallics 1 ,3-dipolar cycloadditions Bisphosphonates Cycloadditions Functionalized compounds Michael addition reactions Rearrangement reactions Synthetic intermediates Addition reactions amine azide azomethine ylide bisphosphonic acid derivative nitrile oxide nitrone derivative phosphonic acid derivative phosphorus tetraethyl vinylidenebisphosphonate thiol unclassified drug chemical structure concentration (parameters) cyclization cycloaddition enantioselectivity epoxidation Michael addition oxidation reduction reaction physical chemistry review stereochemistry structure analysis
Acceso en línea:	https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00397881_v46_n9_p1129_Rodriguez http://hdl.handle.net/20.500.12110/paper_00397881_v46_n9_p1129_Rodriguez
Aporte de:	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires

id	paper:paper_00397881_v46_n9_p1129_Rodriguez
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spelling	paper:paper_00397881_v46_n9_p1129_Rodriguez2023-06-08T15:03:38Z Tetraethyl vinylidenebisphosphonate: A versatile synthon for the preparation of bisphosphonates Rodríguez, Juan Bautista 1 3-dipolar cycloadditions bisphosphonates Michael additions tetraethyl vinylidene bisphosphonate Amines Chemical compounds Cycloaddition Nitrogen oxides Nucleophiles Olefins Organometallics 1 ,3-dipolar cycloadditions Bisphosphonates Cycloadditions Functionalized compounds Michael addition reactions Michael additions Rearrangement reactions Synthetic intermediates Addition reactions amine azide azomethine ylide bisphosphonic acid derivative nitrile oxide nitrone derivative phosphonic acid derivative phosphorus tetraethyl vinylidenebisphosphonate thiol unclassified drug chemical structure concentration (parameters) cyclization cycloaddition enantioselectivity epoxidation Michael addition oxidation reduction reaction physical chemistry review stereochemistry structure analysis Tetraethyl vinylidenebisphosphonate is a versatile synthetic intermediate that allows access to a variety of highly functionalized compounds bearing the bisphosphonic moiety. As an electron-deficient alkene, this compound is able to undergo conjugate addition with a variety of reagents including strong nucleophiles, such as organometallic reagents and enolates, as well as very mild nucleophiles, such as amines, mercaptans and alcohols. The title compound also possesses the ability to behave as a dipolarophile or dienophile in 1,3-dipolar cycloadditions or Diels-Alder reactions, giving rise to five- or six-membered rings containing the bisphosphonic unit. In summary, tetraethyl vinylidenebisphosphonate is a very useful synthon to have at hand for straightforward syntheses of bisphosphonate derivatives of diverse structures. This bisphosphonate moiety has proven to be very important to impart important pharmacological action. 1 Introduction 2 General Reactivity 3 Michael Addition Reactions 3.1 Reaction with Organometallic Reagents 3.2 Reaction with Mercaptans and Amines 3.3 Reaction with Phosphorus-Containing Nucleophiles 3.4 Epoxidation, Loss of a Phosphonate Unit and Rearrangement Reactions 3.5 Michael Reactions with Enolates 4. Cycloaddition Reactions 4.1 Diels-Alder Reactions 4.2 1,3-Dipolar Cycloadditions 4.2.1 Reaction with Diazo Compounds 4.2.2 Reaction with Nitrones 4.2.3 Reaction with Nitrile Oxides 4.2.4 Grigg Azomethine Ylide Cyclizations 4.2.5 Reaction with Azides 5 Concluding Remarks. © Georg Thieme Verlag Stuttgart, New York. Fil:Rodriguez, J.B. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. 2014 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00397881_v46_n9_p1129_Rodriguez http://hdl.handle.net/20.500.12110/paper_00397881_v46_n9_p1129_Rodriguez
institution	Universidad de Buenos Aires
institution_str	I-28
repository_str	R-134
collection	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic	1 3-dipolar cycloadditions bisphosphonates Michael additions tetraethyl vinylidene bisphosphonate Amines Chemical compounds Cycloaddition Nitrogen oxides Nucleophiles Olefins Organometallics 1 ,3-dipolar cycloadditions Bisphosphonates Cycloadditions Functionalized compounds Michael addition reactions Michael additions Rearrangement reactions Synthetic intermediates Addition reactions amine azide azomethine ylide bisphosphonic acid derivative nitrile oxide nitrone derivative phosphonic acid derivative phosphorus tetraethyl vinylidenebisphosphonate thiol unclassified drug chemical structure concentration (parameters) cyclization cycloaddition enantioselectivity epoxidation Michael addition oxidation reduction reaction physical chemistry review stereochemistry structure analysis
spellingShingle	1 3-dipolar cycloadditions bisphosphonates Michael additions tetraethyl vinylidene bisphosphonate Amines Chemical compounds Cycloaddition Nitrogen oxides Nucleophiles Olefins Organometallics 1 ,3-dipolar cycloadditions Bisphosphonates Cycloadditions Functionalized compounds Michael addition reactions Michael additions Rearrangement reactions Synthetic intermediates Addition reactions amine azide azomethine ylide bisphosphonic acid derivative nitrile oxide nitrone derivative phosphonic acid derivative phosphorus tetraethyl vinylidenebisphosphonate thiol unclassified drug chemical structure concentration (parameters) cyclization cycloaddition enantioselectivity epoxidation Michael addition oxidation reduction reaction physical chemistry review stereochemistry structure analysis Rodríguez, Juan Bautista Tetraethyl vinylidenebisphosphonate: A versatile synthon for the preparation of bisphosphonates
topic_facet	1 3-dipolar cycloadditions bisphosphonates Michael additions tetraethyl vinylidene bisphosphonate Amines Chemical compounds Cycloaddition Nitrogen oxides Nucleophiles Olefins Organometallics 1 ,3-dipolar cycloadditions Bisphosphonates Cycloadditions Functionalized compounds Michael addition reactions Michael additions Rearrangement reactions Synthetic intermediates Addition reactions amine azide azomethine ylide bisphosphonic acid derivative nitrile oxide nitrone derivative phosphonic acid derivative phosphorus tetraethyl vinylidenebisphosphonate thiol unclassified drug chemical structure concentration (parameters) cyclization cycloaddition enantioselectivity epoxidation Michael addition oxidation reduction reaction physical chemistry review stereochemistry structure analysis
description	Tetraethyl vinylidenebisphosphonate is a versatile synthetic intermediate that allows access to a variety of highly functionalized compounds bearing the bisphosphonic moiety. As an electron-deficient alkene, this compound is able to undergo conjugate addition with a variety of reagents including strong nucleophiles, such as organometallic reagents and enolates, as well as very mild nucleophiles, such as amines, mercaptans and alcohols. The title compound also possesses the ability to behave as a dipolarophile or dienophile in 1,3-dipolar cycloadditions or Diels-Alder reactions, giving rise to five- or six-membered rings containing the bisphosphonic unit. In summary, tetraethyl vinylidenebisphosphonate is a very useful synthon to have at hand for straightforward syntheses of bisphosphonate derivatives of diverse structures. This bisphosphonate moiety has proven to be very important to impart important pharmacological action. 1 Introduction 2 General Reactivity 3 Michael Addition Reactions 3.1 Reaction with Organometallic Reagents 3.2 Reaction with Mercaptans and Amines 3.3 Reaction with Phosphorus-Containing Nucleophiles 3.4 Epoxidation, Loss of a Phosphonate Unit and Rearrangement Reactions 3.5 Michael Reactions with Enolates 4. Cycloaddition Reactions 4.1 Diels-Alder Reactions 4.2 1,3-Dipolar Cycloadditions 4.2.1 Reaction with Diazo Compounds 4.2.2 Reaction with Nitrones 4.2.3 Reaction with Nitrile Oxides 4.2.4 Grigg Azomethine Ylide Cyclizations 4.2.5 Reaction with Azides 5 Concluding Remarks. © Georg Thieme Verlag Stuttgart, New York.
author	Rodríguez, Juan Bautista
author_facet	Rodríguez, Juan Bautista
author_sort	Rodríguez, Juan Bautista
title	Tetraethyl vinylidenebisphosphonate: A versatile synthon for the preparation of bisphosphonates
title_short	Tetraethyl vinylidenebisphosphonate: A versatile synthon for the preparation of bisphosphonates
title_full	Tetraethyl vinylidenebisphosphonate: A versatile synthon for the preparation of bisphosphonates
title_fullStr	Tetraethyl vinylidenebisphosphonate: A versatile synthon for the preparation of bisphosphonates
title_full_unstemmed	Tetraethyl vinylidenebisphosphonate: A versatile synthon for the preparation of bisphosphonates
title_sort	tetraethyl vinylidenebisphosphonate: a versatile synthon for the preparation of bisphosphonates
publishDate	2014
url	https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00397881_v46_n9_p1129_Rodriguez http://hdl.handle.net/20.500.12110/paper_00397881_v46_n9_p1129_Rodriguez
work_keys_str_mv	AT rodriguezjuanbautista tetraethylvinylidenebisphosphonateaversatilesynthonforthepreparationofbisphosphonates
_version_	1768545274827898880

Tetraethyl vinylidenebisphosphonate: A versatile synthon for the preparation of bisphosphonates

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