The oxa-Michael reaction in the synthesis of 5-and 6-membered oxygen-containing heterocycles

被引：54

作者：

Ahmad, Tauqir ^{[1
]}

Ullah, Nisar ^{[1
]}

机构：

[1] King Fahd Univ Petr & Minerals, Chem Dept, Dhahran 31261, Saudi Arabia

来源：

ORGANIC CHEMISTRY FRONTIERS | 2021年 / 8卷 / 06期

关键词：

DOMINO OXA-MICHAEL/1,6-ADDITION REACTIONS; ORGANOCATALYTIC ASYMMETRIC-SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; DIASTEREOSELECTIVE SYNTHESIS; CONJUGATE ADDITION; ENANTIOSELECTIVE SYNTHESIS; STEREODIVERGENT SYNTHESIS; CASCADE REACTIONS; CARBOXYLIC-ACIDS; AMINO-ALCOHOLS;

D O I：

10.1039/d0qo01312a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The oxa-Michael reaction (OMR) offers the most effective and straightforward route to the synthesis of a wide range of 5- and 6-membered oxygen-containing heterocycles including tetrahydropyrans, tetrahydrofurans, 1,4 dioxanes, isoxazolidines, isoxazolines, gamma-lactones and related gamma-butenolides. These molecular frameworks are frequently featured in numerous biologically active substances. Moreover, the emergence of organocatalytic asymmetric OMR has empowered access to a variety of diverse oxygen-containing heterocycles in a highly enantio- and/or diastereoselective fashion. This review provides an updated account on the recent advances and applications of OMR in the synthesis 5- and 6-membered monocyclic oxo-heterocycles published in the literature since 2013 to date.

引用

页码：1329 / 1344

页数：16

共 76 条

[11] Small-molecule H-bond donors in asymmetric catalysis [J].

Doyle, Abigail G. ;

Jacobsen, Eric N. .

CHEMICAL REVIEWS, 2007, 107 (12) :5713-5743

[12] Stereodivergent synthesis of cyclic γ-aminobutyric acid - GABA analogues [J].

Duris, Andrej ;

Berkes, Dusan ;

Jakubec, Pavol .

TETRAHEDRON LETTERS, 2019, 60 (06) :480-484

[13] DIASTEREOSELECTIVE SYNTHESIS OF PROTECTED SYN 1,3-DIOLS BY BASE-CATALYZED INTRAMOLECULAR CONJUGATE ADDITION OF HEMIACETAL-DERIVED ALKOXIDE NUCLEOPHILES [J].

EVANS, DA ;

GAUCHETPRUNET, JA .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (09) :2446-2453

[14] Asymmetric Cycloetherifications by Bifunctional Aminothiourea Catalysts: The Importance of Hydrogen Bonding [J].

Fukata, Yukihiro ;

Miyaji, Ryota ;

Okamura, Takaaki ;

Asano, Keisuke ;

Matsubara, Seijiro .

SYNTHESIS-STUTTGART, 2013, 45 (12) :1627-1634

[15] Stereoselective Synthesis of 2,6-Cis-Substituted Tetrahydropyrans: Bronsted Acid-Catalyzed Intramolecular Oxa-Conjugate Cyclization of α,β-Unsaturated Ester Surrogates [J].

Fuwa, Haruhiko ;

Ichinokawa, Naoki ;

Noto, Kenkichi ;

Sasaki, Makoto .

JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (06) :2588-2607

[16]

Gamba-SuYnchez D., 2018, SYNTHESIS-STUTTGART, P3997

[17] Tandem Nucleophilic Addition/Oxa-Michael Reaction for the Synthesis of cis-2,6-Disubstituted Tetrahydropyrans [J].

Gharpure, Santosh J. ;

Prasad, J. V. K. ;

Bera, Kalisankar .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (17) :3570-3574

[18] An -Helix-Mimicking 12,13-Helix: Designed//-Foldamers as Selective Inhibitors of Protein-Protein Interactions [J].

Grison, Claire M. ;

Miles, Jennifer A. ;

Robin, Sylvie ;

Wilson, Andrew J. ;

Aitken, David J. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (37) :11096-11100

[19] Oxa-Michael Addition to α,β-Unsaturated Nitriles: An Expedient Route to γ-Amino Alcohols and Derivatives [J].

Guo, Beibei ;

Zijlstra, Douwe S. ;

de Vries, Johannes G. ;

Otten, Edwin .

CHEMCATCHEM, 2018, 10 (13) :2868-2872

[20] Oxa-Michael addition promoted by the aqueous sodium carbonate [J].

Guo, Shi-Huan ;

Xing, Sheng-Zhu ;

Mao, Shuai ;

Gao, Ya-Ru ;

Chen, Wen-Liang ;

Wang, Yong-Qiang .

TETRAHEDRON LETTERS, 2014, 55 (49) :6718-6720

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