Enantioselective Rhodium-Catalyzed Allylation of Cyclic Imines with Potassium Allyltrifluoroborates

被引：57

作者：

Hepburn, Hamish B. ^{[1
]}

Chotsaeng, Nawasit ^{[1
]}

Luo, Yunfei ^{[1
]}

Lam, Hon Wai ^{[1
]}

机构：

[1] Univ Edinburgh, Sch Chem, EaStCHEM, Edinburgh EH9 3JJ, Midlothian, Scotland

来源：

SYNTHESIS-STUTTGART | 2013年 / 45卷 / 19期

基金：

英国工程与自然科学研究理事会; 欧洲研究理事会;

关键词：

allyltrifluoroborates; asymmetric catalysis; enantioselectivity; imines; rhodium; ASYMMETRIC CONJUGATE ALKYNYLATION; PALLADIUM PINCER COMPLEXES; ALLYLGLYCINE DERIVATIVES; HYDRAZONO ESTERS; CHIRAL LIGANDS; ALDEHYDES; 1,4-ADDITION; KETIMINES; ARYLATION; REAGENTS;

D O I：

10.1055/s-0033-1339499

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

This article presents further examples of the enantioselective rhodium-catalyzed addition of potassium allyltrifluoroborates to cyclic imines. A wide range of substituted allyl-trifluoroborates are compatible with this process, and provide protected homoallylic amines with high levels of diastereo- and enantioselection. The reactions display a strong preference for carbon-carbon bond formation at the more substituted terminus of the allyl fragment of the allyltrifluoroborate, regardless of the position of the boron atom. Representative examples of manipulation of the products are also described.

引用

页码：2649 / 2661

页数：13

共 79 条

[1] Synthesis and catalytic application of chiral 1,1′-bi-2-naphthol- and biphenanthrol-based pincer complexes:: Selective allylation of sulfonimines with allyl stannane and allyl trifluoroborate [J].

Aydin, Juhanes ;

Kumar, K. Senthil ;

Sayah, Mahmoud J. ;

Wallner, Olov A. ;

Szabo, Kalman J. .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (13) :4689-4697

[2] Oxaziridine-mediated catalytic hydroxylation of unactivated 3° C-H bonds using hydrogen peroxide [J].

Brodsky, BH ;

Du Bois, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (44) :15391-15393

[3] Indium(I)-Catalyzed Asymmetric Allylation, Crotylation, and α-Chloroallylation of Hydrazones with Rare Constitutional and High Configurational Selectivities [J].

Chakrabarti, Ananya ;

Konishi, Hideyuki ;

Yamaguchi, Miyuki ;

Schneider, Uwe ;

Kobayashi, Shu .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (10) :1838-1841

[4] Hydride as a Leaving Group in the Reaction of Pinacolborane with Halides under Ambient Grignard and Barbier Conditions. One-Pot Synthesis of Alkyl, Aryl, Heteroaryl, Vinyl, and Allyl Pinacolboronic Esters [J].

Clary, Jacob W. ;

Rettenmaier, Terry J. ;

Snelling, Rachel ;

Bryks, Whitney ;

Banwell, Jesse ;

Wipke, W. Todd ;

Singaram, Bakthan .

JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (23) :9602-9610

[5]

Coope J. L., 1998, [No title captured], Patent No. [US5753599, 5753599]

[6] Rhodium-catalyzed enantioselective desymmetrization of bicyclic hydrazines with alkynylboronic esters [J].

Crotti, Stefano ;

Bertolini, Ferruccio ;

Macchia, Franco ;

Pineschi, Mauro .

CHEMICAL COMMUNICATIONS, 2008, (27) :3127-3129

[7] Chiral olefins as steering ligands in asymmetric catalysis [J].

Defieber, Christian ;

Gruetzmacher, Hansjoerg ;

Carreira, Erick M. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (24) :4482-4502

[8] Catalytic enantioselective addition of allylic organometallic reagents to aldehydes and ketones [J].

Denmark, SE ;

Fu, JP .

CHEMICAL REVIEWS, 2003, 103 (08) :2763-2793

[9] Addition of alkynes to aldehydes and activated ketones catalyzed by rhodium-phosphine complexes [J].

Dhondi, Pawan K. ;

Carberry, Patrick ;

Choi, Lydia B. ;

Chishohm, John D. .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (25) :9590-9596

[10] Synthetic applications of rhodium catalysed conjugate addition [J].

Edwards, Hannah J. ;

Hargrave, Jonathan D. ;

Penrose, Stephen D. ;

Frost, Christopher G. .

CHEMICAL SOCIETY REVIEWS, 2010, 39 (06) :2093-2105

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