Enantioselective Friedel-Crafts Alkylation of Indoles with Trifluoroethylidene Malonates by Copper-Bis(oxazoline) Complexes: Construction of Trifluoromethyl-Substituted Stereogenic Tertiary Carbon Center

被引：62

作者：

Wen, Lele ^{[1
]}

Shen, Qilong ^{[1
]}

Wan, Xiaolong ^{[1
]}

Lu, Long ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, Shanghai 200032, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 76卷 / 07期

基金：

中国国家自然科学基金;

关键词：

ALPHA-TRIFLUOROMETHYLATION; HETEROAROMATIC-COMPOUNDS; ASYMMETRIC FLUORINATION; ACID; TRIFLUOROPYRUVATE; NITROALKENES; REACTIVITY; ALDEHYDES;

D O I：

10.1021/jo1024333

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An enantioselective alkylation of indoles with trifluoroethylidene malonates catalyzed by copper(II) bis (oxazoline) complexes has been developed. The expected adducts with a stereogenic tertiary carbon center bearing a trifluoromethyl group were obtained in excellent yields (up to 99%) and ee values (up to 96% ee). The synthetic utility of this asymmetric catalytic reaction was demonstrated by the preparation of beta-CF3-tryptophan and 4-CF3-beta-carboline in high ee.

引用

页码：2282 / 2285

页数：4

共 16 条

[1] Synthesis of Functionalized Indoles with a Trifluoromethyl-Substituted Stereogenic Tertiary Carbon Atom Through an Enantioselective Friedel-Crafts Alkylation with β-Trifluoromethyl-α,β-enones
Blay, Gonzalo
Fernandez, Isabel
Carmen Munoz, M.
Pedro, Jose R.
Vila, Carlos
CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (30) : 9117 - 9122
[2] Enantioselective Friedel-Crafts alkylation of indoles with nitroalkenes catalyzed by a bis(oxazoline)-Cu(II) complex
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Bisai, Alakesh
Singh, Vinod K.
TETRAHEDRON LETTERS, 2007, 48 (07) : 1127 - 1129
[3] Highly enantioselective Friedel-Crafts alkylation of indoles and pyrrole with β,γ-unsaturated α-ketoesters catalyzed by heteroarylidene-tethered bis(oxazoline) copper complexes
Liu, Lei
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Xiao, Yumei
Du, Fengpei
Qin, Zhaohai
Li, Nan
Fu, Bin
CHEMICAL COMMUNICATIONS, 2012, 48 (74) : 9281 - 9283
[4] Enantioselective Friedel-Crafts alkylation of indoles with nitroalkenes catalyzed by bifunctional tridentate bis(oxazoline)-Zn(II) complex
Lu, SF
Du, DM
Xu, JX
ORGANIC LETTERS, 2006, 8 (10) : 2115 - 2118
[5] Chriral Bis(oxazolidine) pyridine-Copper-Catalyzed Enantioselective Friedel-Crafts Alkylation of Indoles with Nitroalkenes
Sato, Toru
Arai, Takayoshi
SYNLETT, 2014, 25 (03) : 349 - 354
[6] Construction of Furan Derivatives with a Trifluoromethyl Stereogenic Center: Enantioselective Friedel-Crafts Alkylations via Formal Trienamine Catalysis
Yang, Guang-Jun
Du, Wei
Chen, Ying-Chun
JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (20): : 10056 - 10061
[7] Enantioselective Friedel-Crafts Alkylation of Indoles with Alkylidene Malonates Catalyzed by N,N′-Dioxide-Scandium(III) Complexes: Asymmetric Synthesis of β-Carbolines
Liu, Yanling
Shang, Deju
Zhou, Xin
Liu, Xiaohua
Feng, Xiaoming
CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (09) : 2055 - 2058
[8] Highly enantioselective Friedel-Crafts reaction of indoles with N-sulfonyl aldimines catalyzed by heteroarylidene malonate-type bis(oxazoline) copper(II) complexes
Liu, Lei
Zhao, Qiuying
Du, Fengpei
Chen, Hongliang
Qin, Zhaohai
Fu, Bin
TETRAHEDRON-ASYMMETRY, 2011, 22 (20-22) : 1874 - 1878
[9] Heteroarylidene-tethered bis(oxazoline) copper complexes catalyzed cascade reaction involving asymmetric Friedel-Crafts alkylation/N-hemiacetalization of indoles with β,γ-unsaturated α-ketoester
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Hou, Xu-He
Zhang, Zhen-Hua
Fu, Bin
TETRAHEDRON, 2015, 71 (22) : 3625 - 3631
[10] Controllable enantioselective Friedel-Crafts reaction between indoles and alkylidene malonates catalyzed by pseudo-C3-symmetric trisoxazoline copper(II) complexes
Zhou, J
Ye, MC
Huang, ZZ
Tang, Y
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (04): : 1309 - 1320

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