Stereoselective Synthesis of Highly Substituted O-Heterocycles via Matteson Homologation: A Ring-Closing Metathesis Approach

被引：2

作者：

Kinsinger, Thorsten ^{[1
]}

Schaefer, Patrick ^{[1
]}

Kazmaier, Uli ^{[1
]}

机构：

[1] Saarland Univ, Organ Chem 1, D-66123 Saarbrucken, Germany

来源：

ORGANIC LETTERS | 2023年 / 25卷 / 18期

关键词：

PROTECTED SIDE-CHAIN; BORONIC ESTERS; NATURAL-PRODUCTS; RUCL2(=CHR)(PR(3))(2); DERIVATIVES; COMPLEXES; MACROLIDE; CATALYSTS;

D O I：

10.1021/acs.orglett.3c01099

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Matteson homologations of chiral boronic esters with the aid of unsaturated nucleophiles are powerful for gaining access to a range of different O-heterocycles via subsequent ring-closing metatheses. Using this protocol, six-to eight-membered rings become available and almost any position of the ring can be substituted and/or functionalized.

引用

页码：3303 / 3307

页数：5

共 50 条

[1] Stereoselective synthesis of five- and six-membered carbocycles via Matteson homologation/ring closing metathesis
Kinsinger, Thorsten
Kazmaier, Uli
ORGANIC CHEMISTRY FRONTIERS, 2023, 10 (12) : 2963 - 2967
[2] Synthesis of Aromatic Heterocycles Using Ring-Closing Metathesis
Potukuchi, Harish K.
Colomer, Ignacio
Donohoe, Timothy J.
HETEROCYCLIC CHEMISTRY IN THE 21ST CENTURY: A TRIBUTE TO ALAN KATRITZKY, VOL 120, 2016, 120 : 43 - 65
[3] Stereoselective Synthesis of Euscapholide and Tetraketide via Prins Cyclisation and Ring-Closing Metathesis
Biradar, Dhanraj O.
Mane, Yogesh D.
Subba Reddy, Basi V.
SYNOPEN, 2022, 06 (04): : 312 - 318
[4] Diastereoselective Synthesis of P-Stereogenic Heterocycles via Enyne Ring-Closing Metathesis
Harvey, James Stephen
Giuffredi, Guy T.
Gouverneur, Veronique
ORGANIC LETTERS, 2010, 12 (06) : 1236 - 1239
[5] Synthesis of N-Substituted Indoles via Aqueous Ring-Closing Metathesis
Sabatino, Valerio
Staub, Dario
Ward, Thomas R.
CATALYSIS LETTERS, 2021, 151 (01) : 1 - 7
[6] Synthesis of cage heterocycles containing tetrahydrofuran and pyran ring system via Grignard addition and ring-closing metathesis
Kotha, Sambasivarao
Cheekatla, Subba Rao
INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 2020, 59 (01): : 75 - 84
[7] Stereoselective synthesis of benzofuran and benzothiophene substituted dihydropyran derivatives via ring closing metathesis
Buyukadali, Nalan Nuriye
Aslan, Nezir
Gumus, Selcuk
Gumus, Aysegul
TETRAHEDRON-ASYMMETRY, 2016, 27 (19) : 954 - 959
[8] A Ring-Closing Metathesis-Based Approach to the Synthesis of (±)-Tetrabenazine
Johannes, Manuel
Altmann, Karl-Heinz
ORGANIC LETTERS, 2012, 14 (14) : 3752 - 3755
[9] Ring-Closing Metathesis Approach to Heteroaromatic Cations: Synthesis of Benzo[a]quinolizinium Salts
Nunez, Ana
Abarca, Beatriz
Cuadro, Ana M.
Alvarez-Builla, Julio
Vaquero, Juan J.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (07) : 1280 - 1290
[10] Ring-closing metathesis of fluoroalkenes toward the synthesis of fluorinated heterocycles containing an oxaza bond
Guerin, David
Dez, Isabelle
Gaumont, Annie-Claude
Pannecoucke, Xavier
Couve-Bonnaire, Samuel
COMPTES RENDUS CHIMIE, 2018, 21 (08) : 740 - 748

← 1 2 3 4 5 →