Enantioselective One-Pot Synthesis of α,β-Epoxy Ketones via Aerobic Oxidation of Cyclopropanols

被引：28

作者：

Elek, Gabor Zoltan ^{[1
]}

Borovkov, Victor ^{[1
]}

Lopp, Margus ^{[1
]}

Kananovich, Dzmitry G. ^{[1
]}

机构：

[1] Tallinn Univ Technol, Dept Chem & Biotechnol, Akad Tee 15, EE-12618 Tallinn, Estonia

来源：

ORGANIC LETTERS | 2017年 / 19卷 / 13期

关键词：

CATALYZED ASYMMETRIC EPOXIDATION; POLYAMINO ACID CATALYSTS; C-H ACTIVATION; ALPHA; BETA-UNSATURATED KETONES; STEREOSELECTIVE EPOXIDATION; CONVENIENT ROUTE; PROTEASOME; ENZYMES; CONVERSION; INHIBITOR;

D O I：

10.1021/acs.orglett.7b01519

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient, mild, and environmentally benign method was developed for the asymmetric synthesis of 2-oxyranyl ketones from easily available tertiary cyclopropanols. The one-pot protocol includes the aerobic oxidation of cyclopropanol derivatives catalyzed by Mn(III) complexes followed by the poly-l-leucine-assisted stereoselective elimination of water from the intermediate peroxides with DBU to afford the corresponding epoxy ketones in high yields and good-to-excellent enantioselectivities (up to 97%).

引用

页码：3544 / 3547

页数：4

共 61 条

[1] A convenient route to 2,6-dialkyl-2,3-dihydro-4H-pyran-4-ones via oxidative cleavage of protected 1-(2-oxoalkyl)-cyclopropanols. Synthesis of (±)-hepialone and its natural congener [J].

Astashko, Dmitry A. ;

Tyvorskii, Vladimir I. .

TETRAHEDRON LETTERS, 2011, 52 (37) :4792-4794

[2] Development of the Julia-Colonna asymmetric epoxidation reaction: Part 1. Preparation and activation of the polyleucine catalyst [J].

Baars, S ;

Drauz, KH ;

Krimmer, HP ;

Roberts, SM ;

Sander, J ;

Skidmore, J ;

Zanardi, G .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2003, 7 (04) :509-513

[3] Preparation of 2,3-epoxycycloalkanones from bicyclo [n.1.0]alkan-1-ols [J].

Barnier, JP ;

Morisson, V ;

Blanco, L .

SYNTHETIC COMMUNICATIONS, 2001, 31 (03) :349-357

[4] Porphyrins as Catalysts in Scalable Organic Reactions [J].

Barona-Castano, Juan C. ;

Carmona-Vargas, Christian C. ;

Brocksom, Timothy J. ;

de Oliveira, Kleber T. .

MOLECULES, 2016, 21 (03)

[5]

Bentley PA, 1997, CHIRALITY, V9, P198, DOI 10.1002/(SICI)1520-636X(1997)9:2<198::AID-CHIR22>3.0.CO

[6]

2-H

[7] Asymmetric enone epoxidation by short solid-phase bound peptides: Further evidence for catalyst helicity and catalytic activity of individual peptide strands [J].

Berkessel, A ;

Koch, B ;

Toniolo, C ;

Rainaldi, M ;

Broxterman, QB ;

Kaptein, B .

BIOPOLYMERS, 2006, 84 (01) :90-96

[8] Polyamino acids as synthetic enzymes: mechanism, applications and relevance to prebiotic catalysis [J].

Carrea, G ;

Colonna, S ;

Kelly, DR ;

Lazcano, A ;

Ottolina, G ;

Roberts, SM .

TRENDS IN BIOTECHNOLOGY, 2005, 23 (10) :507-513

[9]

Cha J., 2012, Organic Reactions, V77, P1, DOI DOI 10.1002/0471264180.or077.01

[10] Selective functionalisation of saturated C-H bonds with metalloporphyrin catalysts [J].

Che, Chi-Ming ;

Lo, Vanessa Kar-Yan ;

Zhou, Cong-Ying ;

Huang, Jie-Sheng .

CHEMICAL SOCIETY REVIEWS, 2011, 40 (04) :1950-1975

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