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Highly enantioselective fluorination of unprotected 3-substituted oxindoles: one-step synthesis of BMS 204352 (MaxiPost).

The catalytic enantioselective fluorination of N-H-free 3-substituted oxindoles was accomplished by a Sc(III)/N,N'-dioxide complex. Under mild reaction conditions, a series of 3-aryl- and 3-alkyl-3-fluoro-2-oxindoles were obtained in excellent yields (up to 98%) and enantioselectivities (up to 99% e... Full description

Journal Title: The Journal of organic chemistry October 19, 2012, Vol.77(20), pp.9148-9155
Main Author: Li, Jun
Other Authors: Cai, Yunfei , Chen, Weiliang , Liu, Xiaohua , Lin, Lili , Feng, Xiaoming
Format: Electronic Article Electronic Article
Language: English
Subjects:
ID: E-ISSN: 1520-6904 ; DOI: 10.1021/jo301705t
Link: http://search.proquest.com/docview/1237085293/?pq-origsite=primo
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title: Highly enantioselective fluorination of unprotected 3-substituted oxindoles: one-step synthesis of BMS 204352 (MaxiPost).
format: Article
creator:
  • Li, Jun
  • Cai, Yunfei
  • Chen, Weiliang
  • Liu, Xiaohua
  • Lin, Lili
  • Feng, Xiaoming
subjects:
  • Crystallography, X-Ray–Chemical Synthesis
  • Indoles–Chemistry
  • Models, Molecular–Chemistry
  • Molecular Structure–Chemistry
  • Oxindoles–Chemistry
  • Stereoisomerism–Chemistry
  • Bms204352
  • Indoles
  • Oxindoles
  • 2-Oxindole
ispartof: The Journal of organic chemistry, October 19, 2012, Vol.77(20), pp.9148-9155
description: The catalytic enantioselective fluorination of N-H-free 3-substituted oxindoles was accomplished by a Sc(III)/N,N'-dioxide complex. Under mild reaction conditions, a series of 3-aryl- and 3-alkyl-3-fluoro-2-oxindoles were obtained in excellent yields (up to 98%) and enantioselectivities (up to 99% ee) by using N-fluorobisbenzenesulfonimide (NFSI) as the fluorination agent. MaxiPost was synthesized efficiently in 81% yield with 96% ee.
language: eng
source:
identifier: E-ISSN: 1520-6904 ; DOI: 10.1021/jo301705t
fulltext: fulltext
issn:
  • 15206904
  • 1520-6904
url: Link


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titleHighly enantioselective fluorination of unprotected 3-substituted oxindoles: one-step synthesis of BMS 204352 (MaxiPost).
creatorLi, Jun ; Cai, Yunfei ; Chen, Weiliang ; Liu, Xiaohua ; Lin, Lili ; Feng, Xiaoming
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ispartofThe Journal of organic chemistry, October 19, 2012, Vol.77(20), pp.9148-9155
identifierE-ISSN: 1520-6904 ; DOI: 10.1021/jo301705t
subjectCrystallography, X-Ray–Chemical Synthesis ; Indoles–Chemistry ; Models, Molecular–Chemistry ; Molecular Structure–Chemistry ; Oxindoles–Chemistry ; Stereoisomerism–Chemistry ; Bms204352 ; Indoles ; Oxindoles ; 2-Oxindole
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descriptionThe catalytic enantioselective fluorination of N-H-free 3-substituted oxindoles was accomplished by a Sc(III)/N,N'-dioxide complex. Under mild reaction conditions, a series of 3-aryl- and 3-alkyl-3-fluoro-2-oxindoles were obtained in excellent yields (up to 98%) and enantioselectivities (up to 99% ee) by using N-fluorobisbenzenesulfonimide (NFSI) as the fluorination agent. MaxiPost was synthesized efficiently in 81% yield with 96% ee.
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titleHighly enantioselective fluorination of unprotected 3-substituted oxindoles: one-step synthesis of BMS 204352 (MaxiPost).
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