Efficient preparation of (S)- and (R)-tert-Butylmethylphosphine-Borane: a novel entry to important P-Stereogenic ligands

A novel one-pot reductive methodol. for the synthesis of optically pure tert-butylmethylphosphine-borane is reported. The prepn. uses as the starting material tert-butylmethylphosphinous acid-borane, which is available in both enantiomeric forms from cis-1,2-aminoindanol and tert-butyldichlorophosph...

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Detalles Bibliográficos
Autores: Salomó i Prat, Ernest, Orgué Gassol, Sílvia, Riera i Escalé, Antoni, Verdaguer i Espaulella, Xavier
Tipo de recurso: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2016
País:España
Institución:Universidad de Barcelona
Repositorio:Dipòsit Digital de la UB
OAI Identifier:oai:diposit.ub.edu:2445/102067
Acceso en línea:https://hdl.handle.net/2445/102067
Access Level:acceso abierto
Palabra clave:Compostos fosforosos
Lligands (Bioquímica)
Phosphorus compounds
Ligands (Biochemistry)
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spelling Efficient preparation of (S)- and (R)-tert-Butylmethylphosphine-Borane: a novel entry to important P-Stereogenic ligandsSalomó i Prat, ErnestOrgué Gassol, SílviaRiera i Escalé, AntoniVerdaguer i Espaulella, XavierCompostos fosforososLligands (Bioquímica)Phosphorus compoundsLigands (Biochemistry)A novel one-pot reductive methodol. for the synthesis of optically pure tert-butylmethylphosphine-borane is reported. The prepn. uses as the starting material tert-butylmethylphosphinous acid-borane, which is available in both enantiomeric forms from cis-1,2-aminoindanol and tert-butyldichlorophosphine. The process is based on the redn. of a mixed anhydride, the configurational stability of which has been studied in several solvents and temps. Tetrabutylammonium borohydride was the best reducing agent allowing for the development of a practical process. To demonstrate the utility of the new methodol., the product obtained in this manner was used in the prepn. of Quinox-P*.Georg Thieme Verlag2016info:eu-repo/semantics/articleinfo:eu-repo/semantics/acceptedVersionapplication/pdfhttps://hdl.handle.net/2445/102067Articles publicats en revistes (Química Inorgànica i Orgànica)reponame:Dipòsit Digital de la UBinstname:Universidad de BarcelonaInglésVersió postprint del document publicat a: http://dx.doi.org/10.1055/s-0035-1561854Synthesis. Journal of Synthetic Organic Chemistry, 2016, vol. 48, num. 16, p. 2659-2663http://dx.doi.org/10.1055/s-0035-1561854(c) Georg Thieme Verlag, 2016info:eu-repo/semantics/openAccessoai:diposit.ub.edu:2445/1020672026-05-27T06:46:51Z
dc.title.none.fl_str_mv Efficient preparation of (S)- and (R)-tert-Butylmethylphosphine-Borane: a novel entry to important P-Stereogenic ligands
title Efficient preparation of (S)- and (R)-tert-Butylmethylphosphine-Borane: a novel entry to important P-Stereogenic ligands
spellingShingle Efficient preparation of (S)- and (R)-tert-Butylmethylphosphine-Borane: a novel entry to important P-Stereogenic ligands
Salomó i Prat, Ernest
Compostos fosforosos
Lligands (Bioquímica)
Phosphorus compounds
Ligands (Biochemistry)
title_short Efficient preparation of (S)- and (R)-tert-Butylmethylphosphine-Borane: a novel entry to important P-Stereogenic ligands
title_full Efficient preparation of (S)- and (R)-tert-Butylmethylphosphine-Borane: a novel entry to important P-Stereogenic ligands
title_fullStr Efficient preparation of (S)- and (R)-tert-Butylmethylphosphine-Borane: a novel entry to important P-Stereogenic ligands
title_full_unstemmed Efficient preparation of (S)- and (R)-tert-Butylmethylphosphine-Borane: a novel entry to important P-Stereogenic ligands
title_sort Efficient preparation of (S)- and (R)-tert-Butylmethylphosphine-Borane: a novel entry to important P-Stereogenic ligands
dc.creator.none.fl_str_mv Salomó i Prat, Ernest
Orgué Gassol, Sílvia
Riera i Escalé, Antoni
Verdaguer i Espaulella, Xavier
author Salomó i Prat, Ernest
author_facet Salomó i Prat, Ernest
Orgué Gassol, Sílvia
Riera i Escalé, Antoni
Verdaguer i Espaulella, Xavier
author_role author
author2 Orgué Gassol, Sílvia
Riera i Escalé, Antoni
Verdaguer i Espaulella, Xavier
author2_role author
author
author
dc.subject.none.fl_str_mv Compostos fosforosos
Lligands (Bioquímica)
Phosphorus compounds
Ligands (Biochemistry)
topic Compostos fosforosos
Lligands (Bioquímica)
Phosphorus compounds
Ligands (Biochemistry)
description A novel one-pot reductive methodol. for the synthesis of optically pure tert-butylmethylphosphine-borane is reported. The prepn. uses as the starting material tert-butylmethylphosphinous acid-borane, which is available in both enantiomeric forms from cis-1,2-aminoindanol and tert-butyldichlorophosphine. The process is based on the redn. of a mixed anhydride, the configurational stability of which has been studied in several solvents and temps. Tetrabutylammonium borohydride was the best reducing agent allowing for the development of a practical process. To demonstrate the utility of the new methodol., the product obtained in this manner was used in the prepn. of Quinox-P*.
publishDate 2016
dc.date.none.fl_str_mv 2016
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/acceptedVersion
format article
status_str acceptedVersion
dc.identifier.none.fl_str_mv https://hdl.handle.net/2445/102067
url https://hdl.handle.net/2445/102067
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv Versió postprint del document publicat a: http://dx.doi.org/10.1055/s-0035-1561854
Synthesis. Journal of Synthetic Organic Chemistry, 2016, vol. 48, num. 16, p. 2659-2663
http://dx.doi.org/10.1055/s-0035-1561854
dc.rights.none.fl_str_mv (c) Georg Thieme Verlag, 2016
info:eu-repo/semantics/openAccess
rights_invalid_str_mv (c) Georg Thieme Verlag, 2016
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv Georg Thieme Verlag
publisher.none.fl_str_mv Georg Thieme Verlag
dc.source.none.fl_str_mv Articles publicats en revistes (Química Inorgànica i Orgànica)
reponame:Dipòsit Digital de la UB
instname:Universidad de Barcelona
instname_str Universidad de Barcelona
reponame_str Dipòsit Digital de la UB
collection Dipòsit Digital de la UB
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15,301603

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