N-Heterocyclic carbene-catalyzed desymmetrization of functionalized 1,4-dienes via Stetter Reaction

被引：31

作者：

Lin, Qiqiao ^{[1
,2
]}

Li, Yuanzhen ^{[1
]}

Das, Deb Kumar ^{[1
]}

Zhang, Guoxiang ^{[1
]}

Zhao, Zhifei ^{[1
]}

Yang, Shuang ^{[1
]}

Fang, Xinqiang ^{[1
]}

机构：

[1] Chinese Acad Sci, Fujian Inst Res Struct Matter, State Key Lab Struct Chem, Fuzhou 350002, Fujian, Peoples R China

[2] Fujian Normal Univ, Fuzhou 350108, Fujian, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2016年 / 52卷 / 38期

基金：

美国国家科学基金会;

关键词：

ENANTIOSELECTIVE SYNTHESIS; ASYMMETRIC-SYNTHESIS; ORGANIC-SYNTHESIS; NHC CATALYSIS; HYDROBENZOFURANONES; CYCLOHEXADIENONES; ORGANOCATALYSIS; STEREOCENTERS;

D O I：

10.1039/c6cc01011c

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The asymmetric desymmetrization of 1,4-dienes via chiral N-heterocyclic carbene catalyzed Stetter-type umpolung reaction was demonstrated. A variety of differently substituted dienes were tolerated very well, affording cyclic ketones with two consecutive stereogenic centers (including one quaternary carbon) in moderate to high yields and with high to excellent enantioselectivities. This work expanded both reaction types of catalytic diene desymmetrizations and sub-strate diversity in NHC catalyzed desymmetric transformations.

引用

页码：6459 / 6462

页数：4

共 56 条

[1] Desymmetrization of a silyl-2,5-cyclohexadiene. Synthesis of (+)-conduritol E and (-)-2-deoxy-allo-inositol [J].

Angelaud, R ;

Landais, Y .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (16) :5202-5203

[2]

[Anonymous], SYNTHESIS

[3]

ASAI M, 1970, CHEM PHARM BULL, V18, P1699

[4] Stereoselective anhydride openings [J].

Atodiresei, Luliana ;

Schiffers, Ingo ;

Bolm, Carsten .

CHEMICAL REVIEWS, 2007, 107 (12) :5683-5712

[5] METABOLITES OF THE FUNGUS ARTHROPSIS-TRUNCATA [J].

AYER, WA ;

CRAW, PA ;

NEARY, J .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1992, 70 (05) :1338-1347

[6] Organocatalytic umpolung: N-heterocyclic carbenes and beyond [J].

Bugaut, Xavier ;

Glorius, Frank .

CHEMICAL SOCIETY REVIEWS, 2012, 41 (09) :3511-3522

[7]

Chiang P.-C., 2011, TCI MAIL, V149, P2

[8]

Clayden J., 2012, Org. Chem. Front, V2nd

[9]

Corey E. J., 2010, Enantioselective Chemical Synthesis: Methods, Logic and Practice

[10] The Catalytic Asymmetric Intramolecular Stetter Reaction [J].

de Alaniz, Javier Read ;

Rovis, Tomislav .

SYNLETT, 2009, (08) :1189-1207

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