Enantioselective Organocatalytic Michael Addition-Cyclization Cascade of Cyclopentane-1,2-dione with Substituted (E)-2-oxobut-3-enoates

被引：7

作者：

Preegel, Gert ^{[1
]}

Ilmarinen, Kaja ^{[1
]}

Jaerving, Ivar ^{[1
]}

Kanger, Tonis ^{[1
]}

Pehk, Tonis ^{[2
]}

Lopp, Margus ^{[1
]}

机构：

[1] Tallinn Univ Technol, Dept Chem, EE-12618 Tallinn, Estonia

[2] NICPB, EE-12618 Tallinn, Estonia

来源：

SYNTHESIS-STUTTGART | 2015年 / 47卷 / 23期

关键词：

organocatalysis; cascade reactions; atropisomerism; stereoselectivity; ALPHA-KETO ESTERS; ASYMMETRIC-SYNTHESIS; HENRY REACTION; DERIVATIVES; EFFICIENT; SQUARAMIDE; CATALYST; 4-HYDROXYCOUMARIN; ATROPISOMERISM; KETOESTERS;

D O I：

10.1055/s-0035-1560347

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An organocatalytic cascade Michael addition-cyclization reaction of cyclopentane-1,2-dione with substituted (E)-2-oxobut-3-enoates, creating two stereocenters and giving bicyclic hemiacetals 3 in excellent yield (up to 93%) and enantioselectivity (up to 96% ee) was developed. From 2-chlorophenyl-substituted (E)-2-oxobut-3-enoate, the adduct revealed pseudo-atropisomerism from the hindered rotation of the phenyl ring. The hemiacetal 3 was reduced with Et3SiH and Lewis acid affording substituted 1,2-cyclopentanedione 8, and disilylated with an excess of TMSOTf and Et3N to the dienol disilyl ether 9.

引用

收藏

页码：3805 / 3812

页数：8

相关论文

共 47 条

[21] A mild, catalytic and efficient Nazarov cyclization mediated by phosphomolybdic acid [J].

Murugan, Kaliyappan ;

Srimurugan, Sankareswaran ;

Chen, Chinpiao .

CHEMICAL COMMUNICATIONS, 2010, 46 (07) :1127-1129

[22] Chiral squaramide-catalyzed asymmetric synthesis of pyranones and pyranonaphthoquinones via cascade reactions of 1,3-dicarbonyls with Morita-Baylis-Hillman acetates of nitroalkenes [J].

Nair, Divya K. ;

Menna-Barreto, Rubem F. S. ;

da Silva Junior, Eufranio N. ;

Mobin, Shaikh M. ;

Namboothiri, Irishi N. N. .

CHEMICAL COMMUNICATIONS, 2014, 50 (53) :6973-6976

[23]

OKI M, 1983, TOP STEREOCHEM, V14, P1

[24] A short enantioselective synthesis of homocitric acid-γ-lactone and 4-hydroxy-homocitric acid-γ-lactones [J].

Paju, A ;

Kanger, T ;

Pehk, T ;

Eek, M ;

Lopp, M .

TETRAHEDRON, 2004, 60 (41) :9081-9084

[25] Asymmetric oxidation of 3-alkyl-1,2-cyclopentanediones.: Part 2:: Oxidative ring cleavage of 3-alkyl-1,2-cyclopentanediones:: synthesis of 2-alkyl-γ-lactone acids [J].

Paju, A ;

Kanger, T ;

Pehk, T ;

Lindmaa, R ;

Müürisepp, AM ;

Lopp, M .

TETRAHEDRON-ASYMMETRY, 2003, 14 (11) :1565-1573

[26] Enantioselective Organocatalytic Michael Addition of Cyclopentane-1,2-diones to Nitroolefins [J].

Preegel, Gert ;

Noole, Artur ;

Ilmarinen, Kaja ;

Jaerving, Ivar ;

Kanger, Tonis ;

Pehk, Tonis ;

Lopp, Margus .

SYNTHESIS-STUTTGART, 2014, 46 (19) :2595-2600

[27] L-Proline catalyzed efficient and convenient synthesis of substituted 2H-chromenes by three-component reaction [J].

Rao, L. Chandrasekhara ;

Meshram, H. M. ;

Kumar, N. Satish ;

Rao, N. Nageswara ;

Babu, N. Jagadeesh .

TETRAHEDRON LETTERS, 2014, 55 (06) :1127-1131

[28] An enantioselective cascade reaction between α, β-unsaturated aldehydes and malonic half-thioesters: a rapid access to chiral δ-lactones [J].

Ren, Qiao ;

Sun, Shaofa ;

Huang, Jiayao ;

Li, Wenjun ;

Wu, Minghu ;

Guo, Haibing ;

Wang, Jian .

CHEMICAL COMMUNICATIONS, 2014, 50 (46) :6137-6140

[29] Chiral indane skeleton based thiourea catalyzed highly stereoselective cascade Michael-enolation-cyclization reaction [J].

Ren, Qiao ;

Gao, Yaojun ;

Wang, Jian .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (14) :5297-5302

[30] Asymmetric organocatalysis: An efficient enantioselective access to benzopyranes and chromenes [J].

Rueping, Magnus ;

Sugiono, Erli ;

Merino, Estibaliz .

CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (21) :6329-6332

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