Organocatalyzed Enantioselective Fluorocyclizations

被引：319

作者：

Lozano, Oscar ^{[1
]}

Blessley, George ^{[1
]}

del Campo, Teresa Martinez ^{[1
]}

Thompson, Amber L. ^{[1
]}

Giuffredi, Guy T. ^{[1
]}

Bettati, Michela ^{[2
]}

Walker, Matthew ^{[2
]}

Borman, Richard ^{[2
]}

Gouverneur, Veronique ^{[1
]}

机构：

[1] Univ Oxford, Chem Res Lab, 12 Mansfield Rd, Oxford OX1 3TA, England

[2] GlaxoSmithKline R&D, Stevenage SG1 2NY, Herts, England

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2011年 / 50卷 / 35期

关键词：

alkaloids; asymmetric catalysis; fluorocyclizations; indoles; organocatalysis; ASYMMETRIC IODOCYCLIZATION; FLUORINATION; IODOCARBOCYCLIZATION; HALOCYCLIZATION; BROMOLACTONIZATION; IODOLACTONIZATION; COMPLEXES;

D O I：

10.1002/anie.201103151

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Enantioenriched fluorinated heterocycles can be prepared through fluorocyclizations of prochiral indoles (see scheme; Ts=tosyl, Bn=benzyl, Boc=tert-butoxycarbonyl). More than twenty examples for this cascade fluorination-cyclization, which is catalyzed by cinchona alkaloids and employs N-fluorobenzenesulfonimide as the electrophilic fluorine source have been explored, and an unprecedented catalytic asymmetric difluorocyclization has also been identified. © 2011 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：8105 / 8109

页数：5

共 55 条

[11] Enantioselective Halocyclization Reactions for the Synthesis of Chiral Cyclic Compounds [J].

Chen, Guofei ;

Ma, Shengming .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (45) :8306-8308

[12] The derivation of non-merohedral twin laws during refinement by analysis of poorly fitting intensity data and the refinement of non-merohedrally twinned crystal structures in the program CRYSTALS [J].

Cooper, RI ;

Gould, RO ;

Parsons, S ;

Watkin, DJ .

JOURNAL OF APPLIED CRYSTALLOGRAPHY, 2002, 35 :168-174

[13] CRYSTALS enhancements: dealing with hydrogen atoms in refinement [J].

Cooper, Richard I. ;

Thompson, Amber L. ;

Watkin, David J. .

JOURNAL OF APPLIED CRYSTALLOGRAPHY, 2010, 43 :1100-1107

[14] Mechanistic evaluation of the halocyclization of 4-penten-1-ol by some bis(2-substituted pyridine) and bis(2,6-disubstituted pyridine)bromonium triflates [J].

Cui, XL ;

Brown, RS .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (18) :5653-5658

[15] Lewis base catalysis of bromo- and iodolactonization, and cycloetherification [J].

Denmark, Scott E. ;

Burk, Matthew T. .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2010, 107 (48) :20655-20660

[16] An approach to enantioselective 5-endo halo-lactonization reactions [J].

Garnier, Jean Marc ;

Robin, Sylvie ;

Rousseau, Gerard .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (20) :3281-3291

[17] The first reagent-controlled asymmetric halolactonizations. Dihydroquinidine-halogen complexes as chiral sources of positive halogen ion [J].

Grossman, RB ;

Trupp, RJ .

CANADIAN JOURNAL OF CHEMISTRY, 1998, 76 (09) :1233-1237

[18] Iodine monochloride-amine complexes: An experimental and computational approach to new chiral electrophiles [J].

Haas, J ;

Bissmire, S ;

Wirth, T .

CHEMISTRY-A EUROPEAN JOURNAL, 2005, 11 (19) :5777-5785

[19] Reagent-controlled stereoselective iodolactonizations [J].

Haas, J ;

Piguel, S ;

Wirth, T .

ORGANIC LETTERS, 2002, 4 (02) :297-300

[20] Catalytic asymmetric iodocarbocyclization reaction [J].

Inoue, T ;

Kitagawa, O ;

Ochiai, O ;

Shiro, M ;

Taguchi, T .

TETRAHEDRON LETTERS, 1995, 36 (51) :9333-9336

← 1 2 3 4 5 6 →