Formation of new phosphates from aldehydes by a DBU-catalysed phospha-Brook rearrangement in a polar solvent
Addition of dialkylphosphites to aromatic aldehydes (Pudovik reaction) by treatment with a base results in two different possible reaction pathways depending on the solvent used. Apolar solvents give the normal Pudovik adduct, whereas the use of DBU in a polar solvent allows the formation of a phosp...
Saved in:
Published in | Synlett no. 15; pp. 2335 - 2336 |
---|---|
Main Authors | , , , |
Format | Journal Article |
Language | English |
Published |
STUTTGART
Thieme Medical Publishers
19.09.2005
|
Subjects | |
Online Access | Get more information |
Cover
Loading…
Abstract | Addition of dialkylphosphites to aromatic aldehydes (Pudovik reaction) by treatment with a base results in two different possible reaction pathways depending on the solvent used. Apolar solvents give the normal Pudovik adduct, whereas the use of DBU in a polar solvent allows the formation of a phosphate ester via phospha-Brook rearrangement of the intermediate hydroxyphosphonate. |
---|---|
AbstractList | Addition of dialkylphosphites to aromatic aldehydes (Pudovik reaction) by treatment with a base results in two different possible reaction pathways depending on the solvent used. Apolar solvents give the normal Pudovik adduct, whereas the use of DBU in a polar solvent allows the formation of a phosphate ester via phospha-Brook rearrangement of the intermediate hydroxyphosphonate. |
Author | Grimaud, L Dos Santos, A El Kaim, L Gaultier, L |
Author_xml | – sequence: 1 givenname: L surname: El Kaim fullname: El Kaim, L email: laurent.elkaim@ensta.fr – sequence: 2 givenname: L surname: Gaultier fullname: Gaultier, L – sequence: 3 givenname: L orcidid: 0000-0003-3904-1822 surname: Grimaud fullname: Grimaud, L – sequence: 4 givenname: A surname: Dos Santos fullname: Dos Santos, A |
BookMark | eNqN0D1PwzAQBmAPRaItjOzekeFsx4kz0kIBqRILnatLcqGBxI7sQJV_T_jame7e06N3uAWbOe-IsQsJVxKMuY5CARhhM5VmMGNzyHUqjJLJKVvE-AogE5vDnLUbHzocGu-4r7mjI-8PPvYHHCjyOviOY1vRYaymWIwc-e1qJ0ocsB0jVX9YrIL3bzwQhoDuhTpyA2_cxHvfYuDRtx_T6Yyd1NhGOv-dS7bb3D2vH8T26f5xfbMVpQY7iJokalloWxmbY1HplHRhk0xlRWrApBJRG5OjylWtdZ3rUlvzhckWKalMLdnlT--RCl_HsiFX0r4PTYdh3AOA0goSY6ZN2knb_-t1M3x_a-3f3aA-AdcJbxs |
CitedBy_id | crossref_primary_10_1002_chem_201201489 crossref_primary_10_1080_10426507_2018_1544132 crossref_primary_10_1002_anie_202116249 crossref_primary_10_1246_cl_170377 crossref_primary_10_1080_10426507_2014_902832 crossref_primary_10_3762_bjoc_18_123 crossref_primary_10_1002_anie_202203650 crossref_primary_10_1021_acs_orglett_0c01765 crossref_primary_10_1021_om2008925 crossref_primary_10_1002_anie_201004879 crossref_primary_10_1021_acs_orglett_3c02563 crossref_primary_10_1002_chin_200605180 crossref_primary_10_1039_D2CC04331A crossref_primary_10_1002_chem_201102207 crossref_primary_10_1021_acs_orglett_1c02907 crossref_primary_10_1021_ol101737b crossref_primary_10_1016_j_tet_2022_132646 crossref_primary_10_1016_j_tetlet_2017_04_002 crossref_primary_10_1039_C8OB00419F crossref_primary_10_1002_ange_202116249 crossref_primary_10_1021_ol501479t crossref_primary_10_1021_acsomega_4c04382 crossref_primary_10_1021_acs_orglett_0c01537 crossref_primary_10_3762_bjoc_17_150 crossref_primary_10_1002_chem_201803218 crossref_primary_10_5059_yukigoseikyokaishi_76_151 crossref_primary_10_1016_j_tetasy_2014_10_018 crossref_primary_10_1002_adsc_201701150 crossref_primary_10_1002_cphc_201100745 crossref_primary_10_1002_ange_201004879 crossref_primary_10_1039_c0sc00268b crossref_primary_10_1080_00397911_2017_1346811 crossref_primary_10_1016_j_jscs_2021_101273 crossref_primary_10_1016_j_molcata_2014_08_004 crossref_primary_10_1246_bcsj_20170040 crossref_primary_10_1002_ejoc_202201101 crossref_primary_10_1039_C6CC06591K crossref_primary_10_1039_C6OB00739B crossref_primary_10_1039_c3sc52913d crossref_primary_10_1021_ol402144q crossref_primary_10_1246_cl_190489 crossref_primary_10_1002_chem_201803809 crossref_primary_10_1016_j_bmcl_2008_10_125 crossref_primary_10_1039_D3GC01565C crossref_primary_10_1002_chem_201800219 crossref_primary_10_1021_acs_orglett_0c00619 crossref_primary_10_1039_C9NJ01867K crossref_primary_10_1002_adsc_200900531 crossref_primary_10_1039_C7OB02059G crossref_primary_10_1002_anie_201007568 crossref_primary_10_1039_c3ob40767e crossref_primary_10_1016_j_tet_2013_11_007 crossref_primary_10_1002_ange_202203650 crossref_primary_10_1016_j_tetlet_2009_10_135 crossref_primary_10_1246_bcsj_20200308 crossref_primary_10_2174_1385272824666200226114306 crossref_primary_10_1002_chem_202002943 crossref_primary_10_1021_jo101743e crossref_primary_10_5059_yukigoseikyokaishi_68_1185 crossref_primary_10_1002_chem_201501377 crossref_primary_10_1039_C4OB01574F crossref_primary_10_1002_slct_202204778 crossref_primary_10_1002_asia_201301650 crossref_primary_10_1002_chem_202201240 crossref_primary_10_1039_D2OB00256F crossref_primary_10_1039_C4RA03269A crossref_primary_10_1039_C5QO00108K crossref_primary_10_1002_ange_201007568 crossref_primary_10_1016_j_tetlet_2015_04_073 crossref_primary_10_1002_chem_201605673 |
Cites_doi | 10.1021/cr960134o |
ContentType | Journal Article |
DBID | 1KM 1KN BLEPL DTL FZXEZ |
DOI | 10.1055/s-2005-872670 |
DatabaseName | Index Chemicus Current Chemical Reactions Web of Science Core Collection Science Citation Index Expanded Web of Science - Science Citation Index Expanded - 2005 |
DatabaseTitle | Web of Science |
DatabaseTitleList | Web of Science |
Database_xml | – sequence: 1 dbid: 1KN name: Current Chemical Reactions url: https://proxy.k.utb.cz/login?url=https://www.webofscience.com/wos/woscc/search-with-editions?editions=WOS.CCR sourceTypes: Enrichment Source Index Database |
DeliveryMethod | no_fulltext_linktorsrc |
Discipline | Chemistry |
EndPage | 2336 |
ExternalDocumentID | 000232045500018 |
GroupedDBID | --- -~X 0R~ 123 1KM 1KN 1UC 4.4 53G AAMFZ ABJNI ABTAH ACGFS ACNCT AEDKO AENEX AFFNX AFZED ALMA_UNASSIGNED_HOLDINGS BLEPL BXHMU CS3 DTL DU5 E.- EWXKU F5P GROUPED_WOS_SCIENCE_CITATION_INDEX_EXPANDED IY8 O9- P-S QTC R.V RIG ROL RTC TN5 WH7 ZE2 ZY4 |
ID | FETCH-LOGICAL-c308t-fe1a31b38d589abd36e3b84727b650561aa3559a292f33f93c3858d58e8b6e272 |
ISICitedReferencesCount | 67 |
ISICitedReferencesURI | https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=CitingArticles&UT=000232045500018 |
ISSN | 0936-5214 |
IngestDate | Fri Oct 18 20:04:05 EDT 2024 Tue Sep 17 23:01:54 EDT 2024 |
IsPeerReviewed | true |
IsScholarly | true |
Issue | 15 |
Keywords | Pudovik reaction phospha-Brook rearrangement dialkylphosphite ACID-ESTERS phosphate esters |
Language | English |
LinkModel | OpenURL |
LogoURL | https://exlibris-pub.s3.amazonaws.com/fromwos-v2.jpg |
MergedId | FETCHMERGED-LOGICAL-c308t-fe1a31b38d589abd36e3b84727b650561aa3559a292f33f93c3858d58e8b6e272 |
ORCID | 0000-0003-3904-1822 |
PageCount | 2 |
ParticipantIDs | webofscience_primary_000232045500018 webofscience_primary_000232045500018CitationCount |
PublicationCentury | 2000 |
PublicationDate | 2005-09-19 |
PublicationDateYYYYMMDD | 2005-09-19 |
PublicationDate_xml | – month: 09 year: 2005 text: 2005-09-19 day: 19 |
PublicationDecade | 2000 |
PublicationPlace | STUTTGART |
PublicationPlace_xml | – name: STUTTGART |
PublicationTitle | Synlett |
PublicationTitleAbbrev | SYNLETT |
PublicationYear | 2005 |
Publisher | Thieme Medical Publishers |
Publisher_xml | – name: Thieme Medical Publishers |
References | PATEL, DV (WOS:A1995TD46600022) 1995; 38 PUOVIK AN (WOS:000232045500018.11) 1969; 39 Rossi, RA (WOS:000180319600004) 2003; 103 KRUTIKOV, VI (WOS:A1986E237800019) 1986; 56 FLOYD AJ (WOS:000232045500018.2) 1970; 20 ABRUZOV BA (WOS:000232045500018.1) 1977; 9 PUDOVIK, AN (WOS:A1979GJ47100001) 1979 FOKIN AV (WOS:000232045500018.3) 1981; 7 PUDOVIK, AN (WOS:A1964WR08200022) 1964; 34 POLEZHAEVA NA (WOS:000232045500018.8) 1986; 8 KONOVALOVA IV (WOS:000232045500018.5) 1991; 61 Rowe, BJ (WOS:000170631200006) 2001; 12 TEXIERBOULLET, F (WOS:A1982PP33000003) 1982 TIMMLER, H (WOS:A1971L030300003) 1971; 104 GALLAGHER, MJ (WOS:A1969E818200064) 1969 |
References_xml | – volume: 34 start-page: 2902 year: 1964 ident: WOS:A1964WR08200022 article-title: REAKTSII DIALKILTIOFOSFORISTYKH KISLOT S NEKOTORYMI KARBONILSODERZHASHCHIMI SOEDINENIYAMI publication-title: ZHURNAL OBSHCHEI KHIMII contributor: fullname: PUDOVIK, AN – volume: 39 start-page: 1018 year: 1969 ident: WOS:000232045500018.11 publication-title: ZH OBSHCH KHIM contributor: fullname: PUOVIK AN – start-page: 2605 year: 1969 ident: WOS:A1969E818200064 article-title: ORGANOPHOSPHORUS INTERMEDIATES .2. REACTION OF TERVALENT PHOSPHORUS COMPOUNDS WITH TETRAPHENYLCYCLOPENTADIENONE publication-title: JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC contributor: fullname: GALLAGHER, MJ – volume: 8 start-page: 1860 year: 1986 ident: WOS:000232045500018.8 publication-title: IZV NAUK SSSR SER KH contributor: fullname: POLEZHAEVA NA – volume: 103 start-page: 71 year: 2003 ident: WOS:000180319600004 article-title: Nucleophilic substitution reactions by electron transfer publication-title: CHEMICAL REVIEWS doi: 10.1021/cr960134o contributor: fullname: Rossi, RA – volume: 104 start-page: 3740 year: 1971 ident: WOS:A1971L030300003 article-title: FORMATION OF PHOSPHORIC ACID ESTERS AND ALPHA-HYDROXYPHOSPHONIC ACID ESTERS BY TREATMENT OF DIALKYL PHOSPHITES WITH AROMATIC KETONES publication-title: CHEMISCHE BERICHTE-RECUEIL contributor: fullname: TIMMLER, H – volume: 38 start-page: 4557 year: 1995 ident: WOS:A1995TD46600022 article-title: ALPHA-HYDROXY PHOSPHINYL-BASED INHIBITORS OF HUMAN RENIN publication-title: JOURNAL OF MEDICINAL CHEMISTRY contributor: fullname: PATEL, DV – volume: 20 start-page: 1735 year: 1970 ident: WOS:000232045500018.2 publication-title: TETRAHEDRON LETT contributor: fullname: FLOYD AJ – start-page: 81 year: 1979 ident: WOS:A1979GJ47100001 article-title: ADDITION-REACTIONS OF ESTERS OF PHOSPHORUS(III) ACIDS WITH UNSATURATED SYSTEMS publication-title: SYNTHESIS-STUTTGART contributor: fullname: PUDOVIK, AN – volume: 61 start-page: 1018 year: 1991 ident: WOS:000232045500018.5 publication-title: ZH OBSHCH KHIM contributor: fullname: KONOVALOVA IV – volume: 7 start-page: 1655 year: 1981 ident: WOS:000232045500018.3 publication-title: IZV AKAD NAUK SSSR S contributor: fullname: FOKIN AV – volume: 9 start-page: 2156 year: 1977 ident: WOS:000232045500018.1 publication-title: IAN SSSR KH contributor: fullname: ABRUZOV BA – volume: 12 start-page: 1701 year: 2001 ident: WOS:000170631200006 article-title: The synthesis of 1-hydroxy phosphonates of high enantiomeric excess using sequential asymmetric reactions: titanium alkoxide-catalyzed P-C bond formation and kinetic resolution publication-title: TETRAHEDRON-ASYMMETRY contributor: fullname: Rowe, BJ – start-page: 916 year: 1982 ident: WOS:A1982PP33000003 article-title: SYNTHESIS OF 1-HYDROXYALKANEPHOSPHONIC ESTERS ON ALUMINA publication-title: SYNTHESIS-STUTTGART contributor: fullname: TEXIERBOULLET, F – volume: 56 start-page: 2027 year: 1986 ident: WOS:A1986E237800019 article-title: INTERACTION OF P(III) ACID-ESTERS WITH 1,5-DIHYDROPERFLUOROPENTANAL HYDRATE .6. ROLE OF SPECIFIC SOLVATION publication-title: ZHURNAL OBSHCHEI KHIMII contributor: fullname: KRUTIKOV, VI |
SSID | ssj0014890 |
Score | 2.1132789 |
Snippet | Addition of dialkylphosphites to aromatic aldehydes (Pudovik reaction) by treatment with a base results in two different possible reaction pathways depending... |
Source | Web of Science |
SourceID | webofscience |
SourceType | Enrichment Source Index Database |
StartPage | 2335 |
SubjectTerms | Chemistry Chemistry, Organic Physical Sciences Science & Technology |
Title | Formation of new phosphates from aldehydes by a DBU-catalysed phospha-Brook rearrangement in a polar solvent |
URI | http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000232045500018 |
WOS | 000232045500018 |
WOSCitedRecordID | wos000232045500018 |
hasFullText | |
inHoldings | 1 |
isFullTextHit | |
isPrint | |
link | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwnV1Lb9QwELa25QAXRHmIAq186C0KJHHiOEfYtlRU5dJdqbfKTmztilWyIgvV8uuZsfOs9rBwiRLLSpzM58nn8TwIOcuiwOQsjHzJQu3HPNC-yg1MPC6NEtIkxnq733znV_P4211yN5k8DKNLNupj_mdnXMn_SBXaQK4YJfsPku1uCg1wDvKFI0gYjnvJ-LKNPLTuGPrBWy-qer1A-ujiRuSq0IttAZfAMqV3_mXuW3vNtgae2XT2YSVe_fB-otMuRhpY74BlCd3XuOz14BV-t94xDYu93ZYg7s5h5mLlXUtXlbkzJX-V6Kno8NA3YmqLX8Wo7byqvVusZFz3ltXWCpGgy8RA180WSxhet7nUu_QPDY6Mw7LXhYy2qEqGupO5xCXNfxgu-U4dHySYDqP27TBEGnFXeWScS_vRP67zPLQJfjAFPxaCCMUBOUgFKsbw-qbbfIqFM821A25Ss8JzP42eupOrWF4ye0GeNwsK-tmh44hMdPmSPJ22dfxekVWHEloZCiihPUooooR2KKFqSyUdoYSOUEJHKKHLErpblNAGJa_J_PJiNr3ymxobfs4CsfGNDmGWKiaKRGRSFYxrpoCxRKniSI5DKYGRZjLKIsOYyViOO8nQWQvFdZRGb8hhWZX6LaEBD6QoMsMlR1qoVc6NSWHGg56PY6GOydnwc92vXTqV-0ciOSbhPt2mTQp7TN2webffrd-TZz12P5AnBvSAPgFSuVGnFgJ_AZqGd-Y |
link.rule.ids | 786 |
linkProvider | Clarivate |
openUrl | ctx_ver=Z39.88-2004&ctx_enc=info%3Aofi%2Fenc%3AUTF-8&rfr_id=info%3Asid%2Fsummon.serialssolutions.com&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=Formation+of+new+phosphates+from+aldehydes+by+a+DBU-catalysed+phospha-Brook+rearrangement+in+a+polar+solvent&rft.jtitle=Synlett&rft.au=El+Kaim%2C+L&rft.au=Gaultier%2C+L&rft.au=Grimaud%2C+L&rft.au=Dos+Santos%2C+A&rft.date=2005-09-19&rft.pub=Thieme+Medical+Publishers&rft.issn=0936-5214&rft.issue=15&rft.spage=2335&rft.epage=2336&rft_id=info:doi/10.1055%2Fs-2005-872670&rft.externalDBID=n%2Fa&rft.externalDocID=000232045500018 |
thumbnail_l | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=0936-5214&client=summon |
thumbnail_m | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=0936-5214&client=summon |
thumbnail_s | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=0936-5214&client=summon |