Efficient synthesis of enantiopure 1,2-bis(hydroxymethyl)-3,3-difluorocyclopropane derivatives through lipase-catalyzed reaction

Efficient synthesis of chiral difluorocyclopropane building block has been accomplished; prochiral diacetate of 1,2-bis(hydroxymethyl)-3, 3-difluorocyclopropane was converted to the corresponding monoacetate through Alcaligenes sp. lipase-catalyzed hydrolysis with >99% enantiomeric excess.

Saved in:
Bibliographic Details
Published inChemistry letters no. 9; pp. 903 - 904
Main Authors Itoh, T, Mitsukura, K, Furutani, M
Format Journal Article
LanguageEnglish
Published TOKYO Chemical Soc Japan 01.09.1998
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
ORGANOFLUORINE COMPOUNDS
Online AccessGet more information

Cover

Abstract Efficient synthesis of chiral difluorocyclopropane building block has been accomplished; prochiral diacetate of 1,2-bis(hydroxymethyl)-3, 3-difluorocyclopropane was converted to the corresponding monoacetate through Alcaligenes sp. lipase-catalyzed hydrolysis with >99% enantiomeric excess.
AbstractList Efficient synthesis of chiral difluorocyclopropane building block has been accomplished; prochiral diacetate of 1,2-bis(hydroxymethyl)-3, 3-difluorocyclopropane was converted to the corresponding monoacetate through Alcaligenes sp. lipase-catalyzed hydrolysis with >99% enantiomeric excess.
Author Furutani, M
Itoh, T
Mitsukura, K
Author_xml – sequence: 1
  givenname: T
  surname: Itoh
  fullname: Itoh, T
– sequence: 2
  givenname: K
  surname: Mitsukura
  fullname: Mitsukura, K
– sequence: 3
  givenname: M
  surname: Furutani
  fullname: Furutani, M
BookMark eNqNkE1LAzEYhINUsK2e_AN7VGxq8ma7H0cp9QMKXvRckuwbN7JNliStrid_ui36AzzNHIYZnpmQkfMOCbnkbM4hL251N-d1Xc1rJk7ImIu8oqzkixEZM1EUtGQAZ2QS4ztjrKoFjMn3yhirLbqUxcGlFqONmTcZOumS9f0uYMZnQJWNV-3QBP85bDG1Q3dNxUzQxppu54PXg-58H3wvHWYNBruXye4xZqkNfvfWZp3tZUSqZZLd8IVNFlDqw4A7J6dGdhEv_nRKXu9XL8tHun5-eFreranOeZWowKYBxk0NCkqWl9yossh1AaBLxTXDRoNgXJXaQF5XDJWqi0VdCGE0k0rDlNz89n6g8iYekTVu-mC3Mgybwx-sLCBncDAAh3T1__TSJnlEWfqdS_ADSEF58g
CitedBy_id crossref_primary_10_3762_bjoc_17_25
crossref_primary_10_1021_cr0100087
crossref_primary_10_1002_ajoc_202300566
crossref_primary_10_1016_S0957_4166_02_00331_2
crossref_primary_10_3987_COM_01_S_K_27
crossref_primary_10_1016_j_jfluchem_2013_06_014
crossref_primary_10_1016_j_jfluchem_2009_06_007
crossref_primary_10_1021_ol000047p
crossref_primary_10_1002_tcr_202300028
crossref_primary_10_1016_S0957_4166_03_00350_1
crossref_primary_10_1002_adsc_200303137
crossref_primary_10_1002_chin_199905079
crossref_primary_10_1016_j_tetasy_2003_11_016
crossref_primary_10_1021_cr010007e
crossref_primary_10_1002_chem_201403737
crossref_primary_10_1016_S0040_4039_99_01088_6
crossref_primary_10_1016_j_jfluchem_2007_05_004
crossref_primary_10_1016_j_jfluchem_2005_12_021
crossref_primary_10_1002_adsc_200303020
crossref_primary_10_1016_S0022_1139_01_00487_0
crossref_primary_10_1016_S0040_4039_99_01366_0
ContentType Journal Article
DBID 1KM
1KN
BLEPL
DTL
FFIDB
DOI 10.1246/cl.1998.903
DatabaseName Index Chemicus
Current Chemical Reactions
Web of Science Core Collection
Science Citation Index Expanded
Web of Science - Science Citation Index Expanded - 1998
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
EISSN 1348-0715
EndPage 904
ExternalDocumentID 000076240200022
FullText_t_NoSnippeting true
GroupedDBID -~X
0R~
1KM
1KN
29B
53G
5GY
6J9
AAPXW
AAUAY
ABCQX
ABEFU
ABTAH
ABXVV
ABZEH
ACGFO
ACIWK
ACNCT
ADIPN
AENEX
AI.
ALMA_UNASSIGNED_HOLDINGS
BCRHZ
BLEPL
CS3
DTL
DU5
EBS
EJD
F20
G8K
GROUPED_WOS_SCIENCE_CITATION_INDEX_EXPANDED
JSF
JSI
KOP
L7B
OJZSN
OK1
OWPYF
OXVGQ
P2P
RAD
RJT
ROX
SJN
TKC
TWZ
UPT
UQL
VH1
ZE2
ZY4
~02
ID FETCH-LOGICAL-c418t-3edd201f92b270471fb764c622c7b1c0edc2301b7cf24980ebb9659633fc0abc2
ISICitedReferencesCount 28
ISICitedReferencesURI https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=CitingArticles&UT=000076240200022
ISSN 0366-7022
IngestDate Wed Sep 18 05:31:12 EDT 2024
Fri Oct 25 20:23:09 EDT 2024
IsPeerReviewed true
IsScholarly true
Issue 9
Keywords ORGANOFLUORINE COMPOUNDS
Language English
LinkModel OpenURL
LogoURL https://exlibris-pub.s3.amazonaws.com/fromwos-v2.jpg
MergedId FETCHMERGED-LOGICAL-c418t-3edd201f92b270471fb764c622c7b1c0edc2301b7cf24980ebb9659633fc0abc2
PageCount 2
ParticipantIDs webofscience_primary_000076240200022
webofscience_primary_000076240200022CitationCount
PublicationCentury 1900
PublicationDate 1998-09-01
PublicationDateYYYYMMDD 1998-09-01
PublicationDate_xml – month: 09
  year: 1998
  text: 1998-09-01
  day: 01
PublicationDecade 1990
PublicationPlace TOKYO
PublicationPlace_xml – name: TOKYO
PublicationTitle Chemistry letters
PublicationTitleAbbrev CHEM LETT
PublicationYear 1998
Publisher Chemical Soc Japan
Publisher_xml – name: Chemical Soc Japan
References Tozer, MJ (WOS:A1996UT78400001) 1996; 52
Csuk, R (WOS:000073685200015) 1998; 54
CRABBE, P (WOS:A1973P440300008) 1973; 38
Barrett, AGM (WOS:A1997XK45500020) 1997; 62
Kitazume, T (WOS:A1997BJ92M00003) 1997; 193
CHEN, CS (WOS:A1982PU95400064) 1982; 104
WELCH, JT (WOS:A1987J990500001) 1987; 43
Taguchi, T (WOS:A1997XK06200005) 1997; 53
MITSUKURA K (WOS:000076240200022.13) 1998
HARADA N (WOS:000076240200022.9) 1983
Barrett, AGM (WOS:A1997YD81100029) 1997; 62
OHTANI, I (WOS:A1991FN00500006) 1991; 113
ITOH T (WOS:000076240200022.10) 1998; 283
EGUSA S (WOS:000076240200022.7) 1985; 59
GELB, MH (WOS:A1985AGF5000001) 1985; 24
ITOH T (WOS:000076240200022.11) 1997; 3
RESNATI, G (WOS:A1993MB89900001) 1993; 49
Brahms, DLS (WOS:A1996VA55100003) 1996; 96
References_xml – volume: 38
  start-page: 1478
  year: 1973
  ident: WOS:A1973P440300008
  article-title: CHEMISTRY OF DIFLUOROCYCLOPROPENES - APPLICATION TO SYNTHESIS OF STEROIDAL ALLENES
  publication-title: JOURNAL OF ORGANIC CHEMISTRY
  contributor:
    fullname: CRABBE, P
– volume: 62
  start-page: 4653
  year: 1997
  ident: WOS:A1997XK45500020
  article-title: Studies on mercury(II)-mediated opening of bi- and tercyclopropane arrays
  publication-title: JOURNAL OF ORGANIC CHEMISTRY
  contributor:
    fullname: Barrett, AGM
– volume: 49
  start-page: 9385
  year: 1993
  ident: WOS:A1993MB89900001
  article-title: SYNTHESIS OF CHIRAL AND BIOACTIVE FLUOROORGANIC COMPOUNDS
  publication-title: TETRAHEDRON
  contributor:
    fullname: RESNATI, G
– year: 1998
  ident: WOS:000076240200022.13
  publication-title: 47 ANN M CHEM SOC JA
  contributor:
    fullname: MITSUKURA K
– volume: 52
  start-page: 8619
  year: 1996
  ident: WOS:A1996UT78400001
  article-title: Methods for the synthesis of gem-difluoromethylene compounds
  publication-title: TETRAHEDRON
  contributor:
    fullname: Tozer, MJ
– year: 1983
  ident: WOS:000076240200022.9
  publication-title: CIRCULAR DICHROIC SP
  contributor:
    fullname: HARADA N
– volume: 53
  start-page: 9497
  year: 1997
  ident: WOS:A1997XK06200005
  article-title: Preparation of methylene-gem-difluorocyclopropanes and its reactivity as Michael acceptor
  publication-title: TETRAHEDRON
  contributor:
    fullname: Taguchi, T
– volume: 96
  start-page: 1585
  year: 1996
  ident: WOS:A1996VA55100003
  article-title: Fluorinated carbenes
  publication-title: CHEMICAL REVIEWS
  contributor:
    fullname: Brahms, DLS
– volume: 59
  start-page: 3175
  year: 1985
  ident: WOS:000076240200022.7
  publication-title: B CHEM SOC JPN
  contributor:
    fullname: EGUSA S
– volume: 43
  start-page: 3123
  year: 1987
  ident: WOS:A1987J990500001
  article-title: ADVANCES IN THE PREPARATION OF BIOLOGICALLY-ACTIVE ORGANOFLUORINE COMPOUNDS
  publication-title: TETRAHEDRON
  contributor:
    fullname: WELCH, JT
– volume: 113
  start-page: 4092
  year: 1991
  ident: WOS:A1991FN00500006
  article-title: HIGH-FIELD FT NMR APPLICATION OF MOSHER METHOD - THE ABSOLUTE-CONFIGURATIONS OF MARINE TERPENOIDS
  publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
  contributor:
    fullname: OHTANI, I
– volume: 104
  start-page: 7294
  year: 1982
  ident: WOS:A1982PU95400064
  article-title: QUANTITATIVE-ANALYSES OF BIOCHEMICAL KINETIC RESOLUTIONS OF ENANTIOMERS
  publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
  contributor:
    fullname: CHEN, CS
– volume: 283
  start-page: 11
  year: 1998
  ident: WOS:000076240200022.10
  publication-title: INNOVATIVE SYNTHETIC
  contributor:
    fullname: ITOH T
– volume: 54
  start-page: 6445
  year: 1998
  ident: WOS:000073685200015
  article-title: Synthesis of difluorocyclopropyl carbocyclic homo-nucleosides
  publication-title: TETRAHEDRON
  contributor:
    fullname: Csuk, R
– volume: 193
  start-page: 91
  year: 1997
  ident: WOS:A1997BJ92M00003
  article-title: Enzymatically controlled reactions of organofluorine compounds
  publication-title: ORGANOFLUORINE CHEMISTRY
  contributor:
    fullname: Kitazume, T
– volume: 62
  start-page: 7673
  year: 1997
  ident: WOS:A1997YD81100029
  article-title: Regioselective ring opening of vinylcyclopropanes by hydrogenation with palladium on activated carbon
  publication-title: JOURNAL OF ORGANIC CHEMISTRY
  contributor:
    fullname: Barrett, AGM
– volume: 3
  start-page: 261
  year: 1997
  ident: WOS:000076240200022.11
  publication-title: J MOL CATAL-B ENZYM
  contributor:
    fullname: ITOH T
– volume: 24
  start-page: 1813
  year: 1985
  ident: WOS:A1985AGF5000001
  article-title: FLUORO KETONE INHIBITORS OF HYDROLYTIC ENZYMES
  publication-title: BIOCHEMISTRY
  contributor:
    fullname: GELB, MH
SSID ssj0008932
Score 1.7000282
Snippet Efficient synthesis of chiral difluorocyclopropane building block has been accomplished; prochiral diacetate of 1,2-bis(hydroxymethyl)-3,...
Source Web of Science
SourceID webofscience
SourceType Enrichment Source
Index Database
StartPage 903
SubjectTerms Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
Title Efficient synthesis of enantiopure 1,2-bis(hydroxymethyl)-3,3-difluorocyclopropane derivatives through lipase-catalyzed reaction
URI http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000076240200022
WOS 000076240200022
WOSCitedRecordID wos000076240200022
hasFullText
inHoldings 1
isFullTextHit
isPrint
link http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwnV3LbtNAFB2lsIAN4inKS7MoEqidYM849niJolalKGxope6qeapRLTtK7YW74gf4Z-6MHXcSsghsrMhxbCv36N4zj3MuQgfWxkokTJEoE5wksdCEM26J1FYw14nb-mYwsx_p6UVydjm5HI1-B7uWmlqO1d1WXcn_RBXOQVydSvYfIjvcFE7AZ4gvHCHCcNwpxsfe_8Gt5t-2JTC53lzEuM0t82rh1gYgUU0pDH8hXPy61W7Timsa3RYfaU4YfMmIntuiqaCQtaqoIKFCfnBiqqXve-ZMaVe9fIr5Amoe8TM-7Z1xupdOFhEy3Omqg9xh4ZVCA2f_VlfXa7uyZ_P6trlplmJttvWkWTZ112iqn6nV9yK9PJyTGLwOflbq8AyKfhlkNZamJIs6MfLYdFmXJdwpqSYB4PIgq-YRCwp03vUr_iv3U296rAonwOTj4Tehw_ZG5Rv2I_oF3dQtNHlDoD20l3HPtr_PhrIOxK5bkurfvxd7wlO_BM_cyl88Vzl_ip70gwz8tUPMMzQy5XP0aIjMC_RrQA4ekIMriwPk4PjI4-bTGmo-E3a0HTE4QAzuEYM3EYNXiHmJLk6Oz6enpO_FQVQS85owozVwRZtTSbMIGI2VWZqolFKVyVhFRisYzMYyUxYG9DwyUjqrypQxqyIhFX2FHpRVaV4jTHMBF6SRskwn0lCeikgoqSexjS3w5X10EP6FV4vOduVqI0j7KN7lsmlvde8sHuo3u936LXp8j-p36KGFfGHeA_ms5QcPij_pNInm
link.rule.ids 783
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=Efficient+synthesis+of+enantiopure+1%2C2-bis%28hydroxymethyl%29-3%2C3-difluorocyclopropane+derivatives+through+lipase-catalyzed+reaction&rft.jtitle=Chemistry+letters&rft.au=Itoh%2C+T&rft.au=Mitsukura%2C+K&rft.au=Furutani%2C+M&rft.date=1998-09-01&rft.pub=Chemical+Soc+Japan&rft.issn=0366-7022&rft.eissn=1348-0715&rft.issue=9&rft.spage=903&rft.epage=904&rft_id=info:doi/10.1246%2Fcl.1998.903&rft.externalDBID=n%2Fa&rft.externalDocID=000076240200022
thumbnail_l http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=0366-7022&client=summon
thumbnail_m http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=0366-7022&client=summon
thumbnail_s http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=0366-7022&client=summon