Pd-Catalyzed kinetic resolution of cyclic enol ethers. An enantioselective route to functionalised pyrans

被引：7

作者：

Zirimwabagabo, Jean-Olivier ^{[1
]}

Harrity, Joseph P. A. ^{[1
]}

机构：

[1] Univ Sheffield, Dept Chem, Sheffield S3 7HF, S Yorkshire, England

来源：

CHEMICAL COMMUNICATIONS | 2014年 / 50卷 / 21期

基金：

英国工程与自然科学研究理事会;

关键词：

MEDIATED REARRANGEMENT REACTION; ALLYLIC SUBSTITUTIONS; ASYMMETRIC CATALYSIS; CHIRAL LIGANDS; RING-CONTRACTION; PALLADIUM; PHOSPHINOARYLOXAZOLINES; P; N-LIGANDS; COMPLEXES; SCOPE;

D O I：

10.1039/c4cc00109e

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Functionalised cyclic enol ethers can be recovered with high levels of enantiocontrol after an asymmetric catalytic [1,3]-rearrangement reaction. These compounds can be further elaborated to a series of carbo- and heterocyclic products in good yield and with excellent levels of stereocontrol.

引用

页码：2735 / 2737

页数：3

共 22 条

[1] Controlled Heterocyclization/Cross-Coupling Domino Reaction of β,γ-Allendiols and α-Allenic Esters: Method and Mechanistic Insight for the Preparation of Functionalized Buta-1,3-dienyl Dihydropyrans [J].

Alcaide, Benito ;

Almendros, Pedro ;

Martinez del Campo, Teresa ;

Teresa Quiros, M. ;

Soriano, Elena ;

Marco-Contelles, Jose L. .

CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (42) :14233-14244

[2] Palladium-Catalyzed [1,3]-O-to-C Rearrangement of Pyrans toward Functionalized Cyclohexanones [J].

Brioche, Julien C. R. ;

Barker, Thomas A. ;

Whatrup, David J. ;

Barker, Michael D. ;

Harrity, Joseph P. A. .

ORGANIC LETTERS, 2010, 12 (21) :4832-4835

[3] Investigation of a stereoselective Co-mediated rearrangement reaction [J].

Carbery, DR ;

Reignier, S ;

Miller, ND ;

Adams, H ;

Harrity, JPA .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (11) :4392-4399

[4]

Carbery DR, 2002, ANGEW CHEM INT EDIT, V41, P2584, DOI 10.1002/1521-3773(20020715)41:14<2584::AID-ANIE2584>3.0.CO

[5]

2-I

[6] ASYMMETRIC PALLADIUM-CATALYZED ALLYLIC SUBSTITUTION USING PHOSPHORUS-CONTAINING OXAZOLINE LIGANDS [J].

DAWSON, GJ ;

FROST, CG ;

WILLIAMS, JMJ .

TETRAHEDRON LETTERS, 1993, 34 (19) :3149-3150

[7] Synthesis of gem-difluorocarba-D-glucose:: A step further in sugar mimesis [J].

Deleuze, A ;

Menozzi, C ;

Sollogoub, M ;

Sinay, P .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (48) :6680-6683

[8] Phosphinooxazolines - A new class of versatile, modular P,N-ligands for asymmetric catalysis [J].

Helmchen, G ;

Pfaltz, A .

ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (06) :336-345

[9] Enantioselective palladium-catalyzed allylic substitutions with asymmetric chiral ligands [J].

Helmchen, G .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1999, 576 (1-2) :203-214

[10]

Langer P, 2000, ANGEW CHEM INT EDIT, V39, P3086, DOI 10.1002/1521-3773(20000901)39:17<3086::AID-ANIE3086>3.0.CO

← 1 2 3 →