共 44 条
Enantioselective organocatalytic fluorination using organofluoro nucleophiles
被引:36
作者:

Zhao, Yujun
论文数: 0 引用数: 0
h-index: 0
机构:
Natl Univ Singapore, Dept Chem, Singapore 117543, Singapore Natl Univ Singapore, Dept Chem, Singapore 117543, Singapore

Pan, Yuanhang
论文数: 0 引用数: 0
h-index: 0
机构:
Natl Univ Singapore, Dept Chem, Singapore 117543, Singapore Natl Univ Singapore, Dept Chem, Singapore 117543, Singapore

Sim, Sui-Boon Derek
论文数: 0 引用数: 0
h-index: 0
机构:
Natl Univ Singapore, Dept Chem, Singapore 117543, Singapore Natl Univ Singapore, Dept Chem, Singapore 117543, Singapore

Tan, Choon-Hong
论文数: 0 引用数: 0
h-index: 0
机构:
Natl Univ Singapore, Dept Chem, Singapore 117543, Singapore
Henan Univ, Key Lab Nat Med & Immunoengn Henan Prov, Kaifeng 475004, Henan, Peoples R China Natl Univ Singapore, Dept Chem, Singapore 117543, Singapore
机构:
[1] Natl Univ Singapore, Dept Chem, Singapore 117543, Singapore
[2] Henan Univ, Key Lab Nat Med & Immunoengn Henan Prov, Kaifeng 475004, Henan, Peoples R China
关键词:
QUATERNARY PHOSPHONIUM SALTS;
ASYMMETRIC ALDOL REACTIONS;
MANNICH-TYPE REACTIONS;
CONJUGATE ADDITION;
ELECTROPHILIC FLUORINATION;
MICHAEL ADDITION;
KETO ESTERS;
PHASE;
FLUOROBIS(PHENYLSULFONYL)METHANE;
AMINATION;
D O I:
10.1039/c1ob05840a
中图分类号:
O62 [有机化学];
学科分类号:
070303 ;
081704 ;
摘要:
Synthetic fluorinated compounds are enormously useful in areas such as materials, agrochemicals, pharmaceuticals and fine chemicals. While methods of electrophilic fluorination have been extensively developed to stereoselectively install fluorine atoms onto molecules, nucleophilic fluorination is a much less explored approach. Recently, several organofluoro reagents have been designed and used as nucleophiles in the asymmetric synthesis of fluorinated compounds, significantly expanding the scope of enantio-enriched fluorine-containing compounds that can be synthesised. Such organofluoro nucleophiles are particularly useful in organocatalytic transformations. In this review, recent advances in the application of organofluoro nucleophiles in organocatalysis are summarised.
引用
收藏
页码:479 / 485
页数:7
相关论文
共 44 条
- [1] Formal Highly Enantioselective Organocatalytic Addition of Fluoromethyl Anion to α,β-Unsaturated Aldehydes[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (29) : 7035 - 7038Alba, Andrea-Nekane论文数: 0 引用数: 0 h-index: 0机构: Univ Barcelona, Dept Organ Chem, Marti & Franques 1-11, E-08028 Barcelona, Spain Univ Barcelona, Dept Organ Chem, Marti & Franques 1-11, E-08028 Barcelona, SpainCompanyo, Xavier论文数: 0 引用数: 0 h-index: 0机构: Univ Barcelona, Dept Organ Chem, Marti & Franques 1-11, E-08028 Barcelona, Spain Univ Barcelona, Dept Organ Chem, Marti & Franques 1-11, E-08028 Barcelona, SpainMoyano, Albert论文数: 0 引用数: 0 h-index: 0机构: Univ Barcelona, Dept Organ Chem, Marti & Franques 1-11, E-08028 Barcelona, Spain Univ Barcelona, Dept Organ Chem, Marti & Franques 1-11, E-08028 Barcelona, SpainRios, Ramon论文数: 0 引用数: 0 h-index: 0机构: Univ Barcelona, Dept Organ Chem, Marti & Franques 1-11, E-08028 Barcelona, Spain Univ Barcelona, Dept Organ Chem, Marti & Franques 1-11, E-08028 Barcelona, Spain
- [2] Asymmetric alkylation reaction of α-fluorotetralone under phase-transfer catalyzed conditions[J]. TETRAHEDRON LETTERS, 1999, 40 (37) : 6785 - 6789Arai, S论文数: 0 引用数: 0 h-index: 0机构: Nagoya City Univ, Fac Pharmaceut Sci, Mizuho Ku, Nagoya, Aichi 4678603, Japan Nagoya City Univ, Fac Pharmaceut Sci, Mizuho Ku, Nagoya, Aichi 4678603, JapanOku, M论文数: 0 引用数: 0 h-index: 0机构: Nagoya City Univ, Fac Pharmaceut Sci, Mizuho Ku, Nagoya, Aichi 4678603, Japan论文数: 引用数: h-index:机构:Shioiri, T论文数: 0 引用数: 0 h-index: 0机构: Nagoya City Univ, Fac Pharmaceut Sci, Mizuho Ku, Nagoya, Aichi 4678603, Japan
- [3] Enantioselective Pd-catalyzed allylation reaction of fluorinated silyl enol ethers[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (05) : 1034 - 1035Belanger, Etienne论文数: 0 引用数: 0 h-index: 0机构: Univ Laval, Canada Res Chair Organ & Med Chem, Dept Chim, Quebec City, PQ G1K 7P4, Canada Univ Laval, Canada Res Chair Organ & Med Chem, Dept Chim, Quebec City, PQ G1K 7P4, CanadaCantin, Katy论文数: 0 引用数: 0 h-index: 0机构: Univ Laval, Canada Res Chair Organ & Med Chem, Dept Chim, Quebec City, PQ G1K 7P4, Canada Univ Laval, Canada Res Chair Organ & Med Chem, Dept Chim, Quebec City, PQ G1K 7P4, CanadaMesse, Olivier论文数: 0 引用数: 0 h-index: 0机构: Univ Laval, Canada Res Chair Organ & Med Chem, Dept Chim, Quebec City, PQ G1K 7P4, Canada Univ Laval, Canada Res Chair Organ & Med Chem, Dept Chim, Quebec City, PQ G1K 7P4, CanadaTremblay, Melanie论文数: 0 引用数: 0 h-index: 0机构: Univ Laval, Canada Res Chair Organ & Med Chem, Dept Chim, Quebec City, PQ G1K 7P4, Canada Univ Laval, Canada Res Chair Organ & Med Chem, Dept Chim, Quebec City, PQ G1K 7P4, CanadaPaquin, Jean-Francois论文数: 0 引用数: 0 h-index: 0机构: Univ Laval, Canada Res Chair Organ & Med Chem, Dept Chim, Quebec City, PQ G1K 7P4, Canada Univ Laval, Canada Res Chair Organ & Med Chem, Dept Chim, Quebec City, PQ G1K 7P4, Canada
- [4] Highly enantioselective fluoromalonate addition to α,β-unsaturated aldehydes[J]. TETRAHEDRON LETTERS, 2009, 50 (35) : 5021 - 5024Companyo, Xavier论文数: 0 引用数: 0 h-index: 0机构: Univ Barcelona, Dept Quim Organ, Fac Quim, E-08028 Barcelona, Catalonia, Spain Charles Univ Prague, Dept Organ Chem, Prague 12800, Czech RepublicHejnova, Monika论文数: 0 引用数: 0 h-index: 0机构: Charles Univ Prague, Dept Organ Chem, Prague 12800, Czech Republic Charles Univ Prague, Dept Organ Chem, Prague 12800, Czech Republic论文数: 引用数: h-index:机构:Vesely, Jan论文数: 0 引用数: 0 h-index: 0机构: Charles Univ Prague, Dept Organ Chem, Prague 12800, Czech Republic Charles Univ Prague, Dept Organ Chem, Prague 12800, Czech RepublicMoyano, Albert论文数: 0 引用数: 0 h-index: 0机构: Univ Barcelona, Dept Quim Organ, Fac Quim, E-08028 Barcelona, Catalonia, Spain Charles Univ Prague, Dept Organ Chem, Prague 12800, Czech RepublicRios, Ramon论文数: 0 引用数: 0 h-index: 0机构: Univ Barcelona, Dept Quim Organ, Fac Quim, E-08028 Barcelona, Catalonia, Spain Passeig Lluis Co, Catalan Inst Res & Adv Studies ICREA, Barcelona 08018, Castalonia, Spain Charles Univ Prague, Dept Organ Chem, Prague 12800, Czech Republic
- [5] Enantioselective Synthesis of Functionalized Fluorinated Cyclohexenones via Robinson Annulation Catalyzed by Primary-Secondary Diamines[J]. JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (01) : 117 - 122Cui, Hai-Feng论文数: 0 引用数: 0 h-index: 0机构: Shanghai Inst Organ Chem, Key Lab Synth Chem & Nat Subst, Shanghai 200032, Peoples R ChinaYang, Ying-Quan论文数: 0 引用数: 0 h-index: 0机构: Shanghai Inst Organ Chem, Key Lab Synth Chem & Nat Subst, Shanghai 200032, Peoples R ChinaChai, Zhuo论文数: 0 引用数: 0 h-index: 0机构: Shanghai Inst Organ Chem, Key Lab Synth Chem & Nat Subst, Shanghai 200032, Peoples R ChinaLi, Peng论文数: 0 引用数: 0 h-index: 0机构: Shanghai Inst Organ Chem, Key Lab Synth Chem & Nat Subst, Shanghai 200032, Peoples R ChinaZheng, Chang-Wu论文数: 0 引用数: 0 h-index: 0机构: Shanghai Inst Organ Chem, Key Lab Synth Chem & Nat Subst, Shanghai 200032, Peoples R ChinaZhu, Shi-Zheng论文数: 0 引用数: 0 h-index: 0机构: Shanghai Inst Organ Chem, Key Lab Synth Chem & Nat Subst, Shanghai 200032, Peoples R China Shanghai Inst Organ Chem, Key Lab Synth Chem & Nat Subst, Shanghai 200032, Peoples R ChinaZhao, Gang论文数: 0 引用数: 0 h-index: 0机构: Shanghai Inst Organ Chem, Key Lab Synth Chem & Nat Subst, Shanghai 200032, Peoples R China
- [6] Highly enantioselective synthesis of α-fluoro-α-nitro esters via organocatalyzed asymmetric Michael addition[J]. TETRAHEDRON, 2011, 67 (02) : 312 - 317Cui, Hai-Peng论文数: 0 引用数: 0 h-index: 0机构: Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Synthet Chem Nat Subst, Shanghai 200032, Peoples R China Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, Shanghai 200032, Peoples R China Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Synthet Chem Nat Subst, Shanghai 200032, Peoples R ChinaLi, Peng论文数: 0 引用数: 0 h-index: 0机构: Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Synthet Chem Nat Subst, Shanghai 200032, Peoples R China Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, Shanghai 200032, Peoples R China Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Synthet Chem Nat Subst, Shanghai 200032, Peoples R ChinaWang, Xiao-Wei论文数: 0 引用数: 0 h-index: 0机构: Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Synthet Chem Nat Subst, Shanghai 200032, Peoples R China Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, Shanghai 200032, Peoples R China Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Synthet Chem Nat Subst, Shanghai 200032, Peoples R ChinaChai, Zhuo论文数: 0 引用数: 0 h-index: 0机构: Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Synthet Chem Nat Subst, Shanghai 200032, Peoples R China Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, Shanghai 200032, Peoples R China Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Synthet Chem Nat Subst, Shanghai 200032, Peoples R ChinaYang, Ying-Quan论文数: 0 引用数: 0 h-index: 0机构: Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Synthet Chem Nat Subst, Shanghai 200032, Peoples R China Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, Shanghai 200032, Peoples R China Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Synthet Chem Nat Subst, Shanghai 200032, Peoples R ChinaCai, Yue-Peng论文数: 0 引用数: 0 h-index: 0机构: S China Normal Univ, Sch Chem & Environm, Key Lab Technol Electrochem Energy Storage & Powe, Guangzhou 510006, Guangdong, Peoples R China Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Synthet Chem Nat Subst, Shanghai 200032, Peoples R ChinaZhu, Shi-Zheng论文数: 0 引用数: 0 h-index: 0机构: Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Synthet Chem Nat Subst, Shanghai 200032, Peoples R China Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, Shanghai 200032, Peoples R China Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Synthet Chem Nat Subst, Shanghai 200032, Peoples R ChinaZhao, Gang论文数: 0 引用数: 0 h-index: 0机构: Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Synthet Chem Nat Subst, Shanghai 200032, Peoples R China Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, Shanghai 200032, Peoples R China Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Synthet Chem Nat Subst, Shanghai 200032, Peoples R China
- [7] Fluorinated carbanions[J]. CHEMICAL REVIEWS, 1996, 96 (05) : 1633 - 1640Farnham, WB论文数: 0 引用数: 0 h-index: 0机构: DuPont Central Research and Development, Wilmington, DE 19880-0328, P. O. Box 80328, Experimental Station
- [8] Fluorobis(phenylsulfonyl)methane: A fluoromethide equivalent and palladium-catalyzed enantioselective allylic monofluoromethylation[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (30) : 4973 - 4977Fukuzumi, Takeo论文数: 0 引用数: 0 h-index: 0机构: Nagoya Inst Technol, Grad Sch Engn, Dept Appl Chem, Nagoya, Aichi 4668555, Japan Nagoya Inst Technol, Grad Sch Engn, Dept Appl Chem, Nagoya, Aichi 4668555, JapanShibata, Norio论文数: 0 引用数: 0 h-index: 0机构: Nagoya Inst Technol, Grad Sch Engn, Dept Appl Chem, Nagoya, Aichi 4668555, Japan Nagoya Inst Technol, Grad Sch Engn, Dept Appl Chem, Nagoya, Aichi 4668555, JapanSugiura, Masayoshi论文数: 0 引用数: 0 h-index: 0机构: Nagoya Inst Technol, Grad Sch Engn, Dept Appl Chem, Nagoya, Aichi 4668555, Japan Nagoya Inst Technol, Grad Sch Engn, Dept Appl Chem, Nagoya, Aichi 4668555, JapanYasui, Hiroyuki论文数: 0 引用数: 0 h-index: 0机构: Nagoya Inst Technol, Grad Sch Engn, Dept Appl Chem, Nagoya, Aichi 4668555, Japan Nagoya Inst Technol, Grad Sch Engn, Dept Appl Chem, Nagoya, Aichi 4668555, Japan论文数: 引用数: h-index:机构:Toru, Takeshi论文数: 0 引用数: 0 h-index: 0机构: Nagoya Inst Technol, Grad Sch Engn, Dept Appl Chem, Nagoya, Aichi 4668555, Japan Nagoya Inst Technol, Grad Sch Engn, Dept Appl Chem, Nagoya, Aichi 4668555, Japan
- [9] Catalytic Enantioselective Michael Addition of 1-Fluoro-bis(phenylsulfonyl)methane to α,β-Unsaturated Ketones Catalyzed by Cinchona Alkaloids[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (42) : 8051 - 8054Furukawa, Tatsuya论文数: 0 引用数: 0 h-index: 0机构: Nagoya Inst Technol, Dept Frontier Mat, Grad Sch Engn, Showa Ku, Nagoya, Aichi 4668555, Japan Nagoya Inst Technol, Dept Frontier Mat, Grad Sch Engn, Showa Ku, Nagoya, Aichi 4668555, JapanShibata, Norio论文数: 0 引用数: 0 h-index: 0机构: Nagoya Inst Technol, Dept Frontier Mat, Grad Sch Engn, Showa Ku, Nagoya, Aichi 4668555, Japan Nagoya Inst Technol, Dept Frontier Mat, Grad Sch Engn, Showa Ku, Nagoya, Aichi 4668555, Japan论文数: 引用数: h-index:机构:论文数: 引用数: h-index:机构:Toru, Takeshi论文数: 0 引用数: 0 h-index: 0机构: Nagoya Inst Technol, Dept Frontier Mat, Grad Sch Engn, Showa Ku, Nagoya, Aichi 4668555, Japan Nagoya Inst Technol, Dept Frontier Mat, Grad Sch Engn, Showa Ku, Nagoya, Aichi 4668555, JapanShiro, Motoo论文数: 0 引用数: 0 h-index: 0机构: Rigaku Corp, Tokyo 1968666, Japan Nagoya Inst Technol, Dept Frontier Mat, Grad Sch Engn, Showa Ku, Nagoya, Aichi 4668555, Japan
- [10] A highly efficient solvent-free asymmetric direct aldol reaction organocatalyzed by recoverable (S)-binam-L-prolinamides.: ESI-MS evidence of the enamine-iminium formation[J]. JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (15) : 5933 - 5943Guillena, Gabriela论文数: 0 引用数: 0 h-index: 0机构: Univ Alicante, Fac Ciencias, Dept Quim Organ, E-03080 Alicante, Spain Univ Alicante, Fac Ciencias, Dept Quim Organ, E-03080 Alicante, Spaindel Carmen Hita, Maria论文数: 0 引用数: 0 h-index: 0机构: Univ Alicante, Fac Ciencias, Dept Quim Organ, E-03080 Alicante, SpainNajera, Carmen论文数: 0 引用数: 0 h-index: 0机构: Univ Alicante, Fac Ciencias, Dept Quim Organ, E-03080 Alicante, SpainViozquez, Santiago F.论文数: 0 引用数: 0 h-index: 0机构: Univ Alicante, Fac Ciencias, Dept Quim Organ, E-03080 Alicante, Spain