Stereoselective C-Glycosylation Reactions with Arylzinc Reagents

被引：114

作者：

Lemaire, Sebastien ^{[1
]}

Houpis, Ioannis N. ^{[1
]}

Xiao, Tingting ^{[3
]}

Li, Juanjuan ^{[3
]}

Digard, Eric ^{[1
]}

Gozlan, Charlotte ^{[1
]}

Liu, Renmao ^{[3
]}

Gavryushin, Andrey ^{[2
]}

Diene, Coura ^{[2
]}

Wang, Youchu ^{[3
]}

Farina, Vittorio ^{[1
]}

Knochel, Paul ^{[2
]}

机构：

[1] Janssen Pharmaceut, Pharmaceut Dev & Mfg Sci, B-2340 Beerse, Belgium

[2] Univ Munich, Dept Chem & Biochem, D-81377 Munich, Germany

[3] WuxiApptec, Proc Chem, Shanghai 200131, Peoples R China

来源：

ORGANIC LETTERS | 2012年 / 14卷 / 06期

关键词：

CROSS-COUPLING APPROACH; ATE COMPLEXES; GLYCOSIDES; TRIALKYLMANGANATE; DISCOVERY; INHIBITOR; ALKYL;

D O I：

10.1021/ol300220p

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A general, transition-metal-free, highly stereoselective cross-coupling reaction between glycosyl bromides and various arylzinc reagents leading to beta-arylated glycosides is reported. The stereoselectivity of the reaction is explained by invoking anchimeric assistance via a bicyclic intermediate. Stereochemical probes confirm the participation of the 2-pivaloyloxy group. Finally, this new method was applied to a short and efficient stereoselective synthesis of Dapagliflozin and Canagliflozin.

引用

页码：1480 / 1483

页数：4

共 43 条

[11] Sn-Free Ni-Catalyzed Reductive Coupling of Glycosyl Bromides with Activated Alkenes [J].

Gong, Hegui ;

Andrews, R. Stephen ;

Zuccarello, Joseph L. ;

Lee, Stephen J. ;

Gagne, Michel R. .

ORGANIC LETTERS, 2009, 11 (04) :879-882

[12] Synthesis of C-aryl-nucleosides and O-aryl-glycosides via cuprate glycosylation [J].

Hainke, Sven ;

Singh, Ishwar ;

Hemmings, Jennifer ;

Seitz, Oliver .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (23) :8811-8819

[13] STEREOSELECTIVE CARBON-CARBON BOND-FORMING REACTION OF 1,1-DIBROMOCYCLOPROPANES VIA 1-HALOCYCLOPROPYLZINCATES [J].

HARADA, T ;

KATSUHIRA, T ;

HATTORI, K ;

OKU, A .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (11) :2958-2965

[14] NOTIZ UBER TETRAACETYL-[4-BROM-N-BUTYL]-BETA-D-GLUCOSID [J].

HELFERICH, B ;

ZIRNER, J .

CHEMISCHE BERICHTE-RECUEIL, 1963, 96 (01) :374-&

[15] Manganese ate complexes as new reducing agents: Perfectly regiocontrolled generation and reactions of the manganese enolates with electrophiles [J].

Hojo, M ;

Harada, H ;

Ito, H ;

Hosomi, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (23) :5459-5460

[16] THE GLYCOSYLATION OF HYDROCARBONS BY MEANS OF THE GRIGNARD REAGENT [J].

HURD, CD ;

BONNER, WA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1945, 67 (11) :1972-1977

[17] REACTIONS OF POLYACYLGLYCOSYL HALIDES WITH GRIGNARD REAGENTS [J].

HURD, CD ;

HOLYSZ, RP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1950, 72 (04) :1732-1735

[18] Reaction of tert-butyl dibromoacetate or N,N-diethyldibromoacetamide with trialkylmanganate providing an alkylated manganese enolate [J].

Inoue, R ;

Shinokubo, H ;

Oshima, K .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (04) :910-911

[19] Dialkylation of gem-dibromocyclopropanes with trialkylmanganate and manganese(II) chloride-catalyzed reaction with alkylmagnesium bromide [J].

Inoue, R ;

Shinokubo, H ;

Oshima, K .

TETRAHEDRON LETTERS, 1996, 37 (30) :5377-5380

[20]

KNOCHEL, 1999, ORGANOZINC REAGENTS

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