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

被引：27

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

[21] The Kulinkovich hydroxycyclopropanation reaction in natural product synthesis [J].

Haym, Isabell ;

Brimble, Margaret A. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (38) :7649-7665

[22]

HELDER R, 1976, TETRAHEDRON LETT, P1831

[23] SYNTHETIC ENZYMES .2. CATALYTIC ASYMMETRIC EPOXIDATION BY MEANS OF POLYAMINO-ACIDS IN A TRIPHASE SYSTEM [J].

JULIA, S ;

GUIXER, J ;

MASANA, J ;

ROCAS, J ;

COLONNA, S ;

ANNUZIATA, R ;

MOLINARI, H .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1982, (06) :1317-1324

[24] "Synthetic Enzymes". Highly Stereoselective Epoxidation of Chalcone in a Triphasic Toluene-Water-Poly[(S)-alanine] System [J].

Julia, S. ;

Vega, J. C. .

AFINIDAD, 2024, 81 (603) :929-931

[25] Macyranones: Structure, Biosynthesis, and Binding Mode of an Unprecedented Epoxyketone that Targets the 20S Proteasome [J].

Keller, Lena ;

Plaza, Alberto ;

Dubiella, Christian ;

Groll, Michael ;

Kaiser, Marcel ;

Mueller, Rolf .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (25) :8121-8130

[26] Oligopeptides as catalysts for asymmetric epoxidation [J].

Kelly, DR ;

Roberts, SM .

BIOPOLYMERS, 2006, 84 (01) :74-89

[27] The isomerisation of (Z)-3-[2H1]-phenylprop-2-enone as a measure of the rate of hydroperoxide addition in Weitz-Scheffer and Julia-Colonna epoxidations [J].

Kelly, DR ;

Caroff, E ;

Flood, RW ;

Heal, W ;

Roberts, SM .

CHEMICAL COMMUNICATIONS, 2004, (18) :2016-2017

[28] Structure and catalytic activity of some soluble polyethylene glycol-peptide conjugates [J].

Kelly, DR ;

Bui, TTT ;

Caroff, E ;

Drake, AF ;

Roberts, SM .

TETRAHEDRON LETTERS, 2004, 45 (20) :3885-3888

[29] The mechanism of polyleucine catalysed asymmetric epoxidation [J].

Kelly, DR ;

Roberts, SM .

CHEMICAL COMMUNICATIONS, 2004, (18) :2018-2020

[30] Fragmentation of tertiary cyclopropanol compounds catalyzed by vanadyl acetylacetonate [J].

Kirihara, M ;

Kakuda, H ;

Ichinose, M ;

Ochiai, Y ;

Takizawa, S ;

Mokuya, A ;

Okubo, K ;

Hatano, A ;

Shiro, M .

TETRAHEDRON, 2005, 61 (20) :4831-4839

← 1 2 3 4 5 6 7 →