Access to chiral γ-butenolides via palladium-catalyzed asymmetric allylic C-H alkylation of 1,4-dienes

被引：26

作者：

Dai, Zhen-Yao ^{[1
,2
]}

Wang, Pu-Sheng ^{[1
,2
]}

Gong, Liu-Zhu ^{[1
,2
,3
]}

机构：

[1] Univ Sci & Technol China, Hefei Natl Lab Phys Sci Microscale, Hefei 230026, Peoples R China

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

[3] Ctr Excellence Mol Synth CAS, Hefei 230026, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2021年 / 57卷 / 55期

关键词：

TERMINAL OLEFINS; BUTYROLACTONES;

D O I：

10.1039/d1cc02295d

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Asymmetric allylic C-H alkylation of 1,4-pentadienes with alpha-angelica lactones has been developed by tri-axial phosphoramidite-palladium catalysis. This reaction can tolerate a range of functional groups under mild conditions, furnishing versatile chiral gamma,gamma-disubstituted butenolides in high yields with good to high levels of stereoselectivity.

引用

页码：6748 / 6751

页数：4

共 37 条

[1] A Sequential Pd-AAA/Cross-Metathesis/Cope Rearrangement Strategy for the Stereoselective Synthesis of Chiral Butenolides [J].

Aubert, Sidonie ;

Katsina, Tania ;

Arseniyadis, Stellios .

ORGANIC LETTERS, 2019, 21 (07) :2231-2235

[2] Toward the development of a general chiral auxiliary. Enantioselective alkylation and a new catalytic asymmetric addition of silyloxyfurans: Application to a total synthesis of (-)-rasfonin [J].

Boeckman, Robert K., Jr. ;

Pero, Joseph E. ;

Boehmler, Debra J. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (34) :11032-11033

[3] Enantioselective butenolide preparation for straightforward asymmetric syntheses of γ-lactones -: Paraconic acids, avenaciolide, and hydroxylated eleutherol [J].

Braukmueller, Stefan ;

Brueckner, Reinhard .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (09) :2110-2118

[4]

Cao XF, 2010, CHINESE J ORG CHEM, V30, P1113

[5] The Vinylogous Aldol and Related Addition Reactions: Ten Years of Progress [J].

Casiraghi, Giovanni ;

Battistini, Lucia ;

Curti, Claudio ;

Rassu, Gloria ;

Zanardi, Franca .

CHEMICAL REVIEWS, 2011, 111 (05) :3076-3154

[6] β-Substituted Alkenyl Heteroarenes as Dipolarophiles in the Cu(I)-atalyzed Asymmetric 1,3-Dipolar Cycloaddition of Azomethine Ylides Empowered by a Dual Activation Strategy: Stereoselectivity and Mechanistic Insight [J].

Chang, Xin ;

Yang, Yuhong ;

Shen, Chong ;

Xue, Kun-Shan ;

Wang, Zuo-Fei ;

Cong, Hengjiang ;

Tao, Hai-Yan ;

Chung, Lung Wa ;

Wang, Chun-Jiang .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2021, 143 (09) :3519-3535

[7] Catalytic asymmetric allylic and homoallylic diamination of terminal olefins via formal C-H activation [J].

Du, Haifeng ;

Zhao, Baoguo ;

Shi, Yian .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (27) :8590-+

[8] Palladium-Catalyzed Asymmetric Allylic C-H Alkylation of 1,4-Dienes with Cyclic β-Keto Esters [J].

Fan, Lian-Feng ;

Wang, Tian-Ci ;

Wang, Pu-Sheng ;

Gong, Liu-Zhu .

ORGANOMETALLICS, 2019, 38 (20) :4014-4021

[9] Nucleophile Coordination Enabled Regioselectivity in Palladium-Catalyzed Asymmetric Allylic C-H Alkylation [J].

Fan, Lian-Feng ;

Luo, Shi-Wei ;

Chen, Shu-Sen ;

Wang, Tian-Ci ;

Wang, Pu-Sheng ;

Gong, Liu-Zhu .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (47) :16806-16810

[10] Monodentate Phosphorus Ligand-Enabled General Palladium-Catalyzed Allylic C-H Alkylation of Terminal Alkenes [J].

Fan, Lian-Feng ;

Wang, Pu-Sheng ;

Gong, Liu-Zhu .

ORGANIC LETTERS, 2019, 21 (17) :6720-6725

← 1 2 3 4 →