Electrophilic Fluorocyclization of Allyl Silanes

被引：77

作者：

Wilkinson, Susan C. ^{[1
]}

Lozano, Oscar ^{[1
]}

Schuler, Marie ^{[1
]}

Pacheco, Maria C. ^{[1
]}

Salmon, Roger ^{[2
]}

Gouverneur, Veronique ^{[1
]}

机构：

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

[2] Syngenta Ltd, Jealotts Hill Int Res Ctr, Bracknell RG42 6YA, Berks, England

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2009年 / 48卷 / 38期

基金：

英国工程与自然科学研究理事会;

关键词：

allyl silanes; asymmetric synthesis; cyclization; fluorination; oxidative cleavage; STEREOSELECTIVE-SYNTHESIS; NORBORNENECARBOXYLIC ACIDS; ALLYLSILANES; FLUORINATION; FLUORIDES; FLUOROLACTONIZATION; TETRAHYDROFURANS; IODOCYCLIZATION; ALLENYLSILANES; F-TEDA-BF4;

D O I：

10.1002/anie.200901795

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A refreshing cascade: General fluorocyclization reactions will breathe new life into the use of fluorinated hetero- and carbocycles as pharmaceuticals and agrochemicals. Allyl silanes have now been shown to undergo fluorinationcyclization with N-F reagents to give cis- and transsubstituted fluorinated heterocycles selectively (see scheme). The correct choice of silyl group was critical to prevent competitive fluorodesilylation. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：7083 / 7086

页数：4

共 33 条

[1] Allyldiisopropylphenylsilane as a synthetic equivalent of 2-hydroxy-1,3-dipole. Stereoselective synthesis of cyclopentanols [J].

Akiyama, T ;

Hoshi, E ;

Fujiyoshi, S .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (14) :2121-2122

[2] Stereoselective synthesis of tetrahydrofurans via formal [3+2]-cycloaddition of aldehydes and allylsilanes. Formal total synthesis of the muscarine alkaloids (-)-allomuscarine and (+)-epimuscarine [J].

Angle, SR ;

El-Said, NA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (14) :3608-3613

[3] Model studies of the overall 5-endo-trig iodocyclization of homoallylic alcohols [J].

Bedford, SB ;

Bell, KE ;

Bennett, F ;

Hayes, CJ ;

Knight, DW ;

Shaw, DE .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (15) :2143-2153

[4] STEREOCONTROLLED CYCLOFUNCTIONALIZATIONS OF DOUBLE-BONDS THROUGH HETEROCYCLIC INTERMEDIATES [J].

CARDILLO, G ;

ORENA, M .

TETRAHEDRON, 1990, 46 (10) :3321-3408

[5] Stereospecific anti SE2′ fluorination of allenylsilanes:: synthesis of enantioenriched propargylic fluorides [J].

Carroll, Laurence ;

McCullough, Samantha ;

Rees, Tom ;

Claridge, Timothy D. W. ;

Gouverneur, Veronique .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2008, 6 (10) :1731-1733

[6] THE PHENYLDIMETHYLSILYL GROUP AS A MASKED HYDROXY GROUP [J].

FLEMING, I ;

HENNING, R ;

PARKER, DC ;

PLAUT, HE ;

SANDERSON, PEJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (04) :317-337

[7]

Greedy, 2003, ANGEW CHEM, V115, P3413

[8] Regio- and enantioselective synthesis of allylic fluorides by electrophilic fluorodesilylation of allyl silanes [J].

Greedy, B ;

Paris, JM ;

Vidal, T ;

Gouverneur, V .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (28) :3291-3294

[9] Cinchona alkaloid catalyzed enantioselective fluorination of allyl silanes, silyl enol ethers, and oxindoles [J].

Ishimaru, Takehisa ;

Shibata, Norio ;

Horikawa, Takao ;

Yasuda, Naomi ;

Nakamura, Shuichi ;

Toru, Takeshi ;

Shiro, Motoo .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (22) :4157-4161

[10] The oxidation of the carbon-silicon bond [J].

Jones, GR ;

Landais, Y .

TETRAHEDRON, 1996, 52 (22) :7599-7662

← 1 2 3 4 →