Iridium-Catalyzed Asymmetric Hydrogenation of γ- and δ-Ketoacids for Enantioselective Synthesis of γ- and δ-Lactones

被引：36

作者：

Hua, Yun-Yu ^{[2
]}

Bin, Huai-Yu ^{[1
]}

Wei, Tao ^{[1
]}

Cheng, Hou-An ^{[2
]}

Lin, Zu-Peng ^{[2
]}

Fu, Xing-Feng ^{[2
]}

Li, Yuan-Qiang ^{[2
]}

Xie, Jian-Hua ^{[1
]}

Yan, Pu-Cha ^{[2
]}

Zhou, Qi-Lin ^{[1
]}

机构：

[1] Nankai Univ, Tianjin, Peoples R China

[2] Zhejiang Raybow Pharmaceut Co Ltd, Taizhou City, Peoples R China

来源：

ORGANIC LETTERS | 2020年 / 22卷 / 03期

基金：

中国国家自然科学基金;

关键词：

GROUP LEADS; EFFICIENT; EZETIMIBE; KETOESTERS; KETO; CONVENIENT; ALKALOIDS; AMINATION; ACID;

D O I：

10.1021/acs.orglett.9b04253

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly efficient asymmetric hydrogenation of gamma- and delta-ketoacids was developed by using a chiral Spiro iridium catalyst (S)-1a, affording the optically active gamma- and delta-hydroxy acids/lactones in high yields with excellent enantioselectivities (up to >99% ee) and turnover numbers (TON up to 100000). This protocol provides an efficient and practical method for enantioselective synthesis of Ezetimibe.

引用

收藏

页码：818 / 822

页数：5

相关论文

共 47 条

[1] Chemoselectivity Control in the Asymmetric Hydrogenation of γ- and δ-Keto Esters into Hydroxy Esters or Diols [J].

Arai, Noriyoshi ;

Namba, Takanori ;

Kawaguchi, Kei ;

Matsumoto, Yuki ;

Ohkuma, Takeshi .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (05) :1386-1389

[2] Selective endothelin a receptor antagonists. 3. Discovery and structure-activity relationships of a series of 4-phenoxybutanoic acid derivatives [J].

Astles, PC ;

Brealey, C ;

Brown, TJ ;

Facchini, V ;

Handscombe, C ;

Harris, NV ;

McCarthy, C ;

McLay, IM ;

Porter, B ;

Roach, AG ;

Sargent, C ;

Smith, C ;

Walsh, RJA .

JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (15) :2732-2744

[3] Ezetimibe [J].

Bays, H .

EXPERT OPINION ON INVESTIGATIONAL DRUGS, 2002, 11 (11) :1587-1604

[4] Effectiveness and tolerability of ezetimibe in patients with primary hypercholesterolemia: Pooled analysis of two phase II studies [J].

Bays, HE ;

Moore, PB ;

Drehobl, MA ;

Rosenblatt, S ;

Toth, PD ;

Dujovne, CA ;

Knopp, RH ;

Lipka, LJ ;

LeBeaut, AP ;

Yang, B ;

Mellars, LE ;

Cuffie-Jackson, C ;

Veltri, EP .

CLINICAL THERAPEUTICS, 2001, 23 (08) :1209-1230

[5] A concise enantioselective synthesis of pyrrolidine sedum alkaloids (R)-(R)-(+), (S)-(S)-(-)-pyrrolsedamine and (S)-(R)-(+)-pyrrolallosedamine by using proline catalysed α-amination reaction [J].

Bhosale, Viraj A. ;

Markad, Sachin B. ;

Waghmode, Suresh B. .

TETRAHEDRON, 2017, 73 (36) :5344-5349

[6] Synthesis and conformational studies of γ-aminoxy peptides [J].

Chen, Fei ;

Song, Ke-Sheng ;

Wu, Yun-Dong ;

Yang, Dan .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (02) :743-755

[7] Enantioselective synthesis of (+)-cryptophycin 52 (LY355703), a potent antimitotic antitumor agent [J].

Ghosh, AK ;

Swanson, L .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (25) :9823-9826

[8] Enantioselective Hydrogenation of Racemic α-Arylamino Lactones to Chiral Amino Diols with Site-Specifically Modified Chiral Spiro Iridium Catalysts [J].

Gu, Xue-Song ;

Yu, Na ;

Yang, Xiao-Hui ;

Zhu, An-Te ;

Xie, Jian-Hua ;

Zhou, Qi-Lin .

ORGANIC LETTERS, 2019, 21 (11) :4111-4115

[9] Recent Progress in Homogeneous Catalytic Hydrogenation of Esters [J].

Gu Xuesong ;

Li Xiaogen ;

Xie Jianhua ;

Zhou Qilin .

ACTA CHIMICA SINICA, 2019, 77 (07) :598-612

[10] Cobalt-catalyzed asymmetric hydroboration of aryl ketones with pinacolborane [J].

Guo, Jun ;

Chen, Jianhui ;

Lu, Zhan .

CHEMICAL COMMUNICATIONS, 2015, 51 (26) :5725-5727

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