Copper-catalyzed regiodivergent 1,4-and 1,6-conjugate silyl addition to diendioates: access to functionalized allylsilanes

被引：13

作者：

Ahmad, Tanveer ^{[1
]}

Li, Qi ^{[1
]}

Qiu, Sheng-Qi ^{[1
]}

Xu, Jian-Lin ^{[1
]}

Xu, Yun-He ^{[1
]}

Loh, Teck-Peng ^{[1
,2
]}

机构：

[1] Univ Sci & Technol China, Dept Chem, Hefei 230026, Anhui, Peoples R China

[2] Nanyang Technol Univ, Sch Phys & Math Sci, Div Chem & Biol Chem, Singapore 637371, Singapore

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2019年 / 17卷 / 25期

基金：

中国国家自然科学基金;

关键词：

SI BOND FORMATION; ASYMMETRIC-SYNTHESIS; CONJUGATE ADDITION; ALPHA; BETA-UNSATURATED ACCEPTORS; ORGANIC-SYNTHESIS; PALLADIUM; SILICON; 1,4-ADDITION; ACTIVATION; CARBONYL;

D O I：

10.1039/c9ob01086f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A copper-catalyzed regioselective 1,4- and 1,6-conjugate addition of a silyl reagent to diendioates was established. Various 1,4- and 1,6-protosilylation products were obtained in good yields and with high regioselectivity via tuning the ligands used in the reactions. This protocol has provided a simple and efficient method for the synthesis of multisubstituted functionalized allylsilanes.

引用

页码：6122 / 6126

页数：5

共 49 条

[1] Copper-free and copper-promoted conjugate addition reactions of bis(triorganosilyl) zincs and tris(triorganosilyl) zincates [J].

Auer, Gertrud ;

Weiner, Barbara ;

Oestreich, Martin .

SYNTHESIS-STUTTGART, 2006, (13) :2113-2116

[2] Allylsilanes and vinylsilanes from silylcupration of carbon-carbon multiple bonds: Scope and synthetic applications [J].

Barbero, A ;

Pulido, FJ .

ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (10) :817-825

[3] Efficient, Enantioselective Assembly of Silanediol Protease Inhibitors [J].

Bo, Yingjian ;

Singh, Swapnil ;

Hoan Quoc Duong ;

Cao, Cui ;

Sieburth, Scott McN .

ORGANIC LETTERS, 2011, 13 (07) :1787-1789

[4] Copper(II)-Catalyzed Silylation of Activated Alkynes in Water: Diastereodivergent Access to E- or Z-b-Silyl-α, β-Unsaturated Carbonyl and Carboxyl Compounds [J].

Calderone, Joseph A. ;

Santos, Webster L. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (16) :4154-4158

[5] Copper(II)-Catalyzed Silyl Conjugate Addition to α,β-Unsaturated Conjugated Compounds: Bronsted Base-Assisted Activation of Si-B Bond in Water [J].

Calderone, Joseph A. ;

Santos, Webster L. .

ORGANIC LETTERS, 2012, 14 (08) :2090-2093

[6] Allylsilanes in organic synthesis - Recent developments [J].

Chabaud, L ;

James, P ;

Landais, Y .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (15) :3173-3199

[7] CHIRAL ORGANOSILICON COMPOUNDS IN ASYMMETRIC-SYNTHESIS [J].

CHAN, TH ;

WANG, D .

CHEMICAL REVIEWS, 1992, 92 (05) :995-1006

[8] Copper-catalyzed silylation reactions of propargyl epoxides: easy access to 2,3-allenols and stereodefined alkenes [J].

Chang, Xi-Hao ;

Liu, Zheng-Li ;

Luo, Yun-Cheng ;

Yang, Chao ;

Liu, Xiao-Wei ;

Da, Bing-Chao ;

Li, Jie-Jun ;

Ahmad, Tanveer ;

Loh, Teck-Peng ;

Xu, Yun-He .

CHEMICAL COMMUNICATIONS, 2017, 53 (67) :9344-9347

[9] Copper(I)-catalyzed disilylation of alkylidene malonates employing a Lewis base activation strategy [J].

Clark, CT ;

Lake, JF ;

Scheidt, KA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (01) :84-85

[10] Copper-Catalyzed Stereo- and Enantioselective 1,4-Protosilylation of α,β-Unsaturated Ketimines To Synthesize Functionalized Allylsilanes [J].

Da, Bing-Chao ;

Liang, Qiu-Ju ;

Luo, Yun-Cheng ;

Ahmad, Tanveer ;

Xu, Yun-He ;

Loh, Teck-Peng .

ACS CATALYSIS, 2018, 8 (07) :6239-6245

← 1 2 3 4 5 →