An Asymmetric Tandem Conjugative Addition-Intramolecular Cyclisation Process to Provide Functionalised 3,6-Dihydropyrans and 4,5-Epoxytetrahydropyrans

被引：24

作者：

Catalan-Munoz, Silvia ^{[1
]}

Mueller, Constanze A. ^{[1
]}

Ley, Steven V. ^{[1
]}

机构：

[1] Univ Cambridge, Dept Chem, Cambridge CB2 1EW, England

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 2010卷 / 01期

基金：

瑞士国家科学基金会;

关键词：

Epoxidation; Organocatalysis; Aldol reactions; Wittig reactions; RING-CLOSING METATHESIS; VINYL SULFONIUM SALTS; DIELS-ALDER REACTIONS; ORGANOCATALYTIC ROUTE; PHOSPHORUS COMPOUNDS; ENANTIOSELECTIVE SYNTHESIS; CHIRAL 1,2-OXAZINES; GENERAL SYNTHESIS; FACILE SYNTHESIS; WITTIG REACTION;

D O I：

10.1002/ejoc.200901145

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of 3,6-dihydropyrans and 4,5-epoxytetrahydropyrans starting from enantiomerically pure beta-hydroxy aldehyde (prepared by an organocatalytic aldol reaction) is described. The key step is a tandem sequence, which consists of a base-promoted conjugative addition to a vinyl on-ium salt, followed by either an intramolecular Wittig process to provide 3,6-dihydropyran derivatives or an intramolecular cyclisation/epoxidation process to afford 4,5-epoxytetrahydropyran scaffolds, The products obtained by this method are common substructures in polyketide natural products.

引用

页码：183 / 190

页数：8

共 70 条

[1] The complexity of catalysis: origins of enantio- and diastereocontrol in sulfur ylide mediated epoxidation reactions [J].

Aggarwal, VK ;

Richardson, J .

CHEMICAL COMMUNICATIONS, 2003, (21) :2644-2651

[2]

BERGELSON LD, 1964, TETRAHEDRON LETT, P2669

[3] NEW METHODS IN PREPARATIVE ORGANIC CHEMISTRY .4. SYNTHESIS OF NATURALLY OCCURRING UNSATURATED FATTY ACIDS BY STERICALLY CONTROLLED CARBONYL OLEFINATION [J].

BERGELSON, LD ;

SHEMYAKIN, MM .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1964, 3 (04) :250-+

[4] STEREOCHEMISTRY OF WITTIG REACTION WITH NON-STABILIZED AND SEMISTABILIZED YLIDS [J].

BERGELSON, LD ;

BARSUKOV, LI ;

SHEMYAKIN, MM .

TETRAHEDRON, 1967, 23 (06) :2709-+

[5]

Berkessel A, 2005, ASYMMETRIC ORGANOCATALYSIS: FROM BIOMIMETIC CONCEPTS TO APPLICATIONS IN ASYMMETRIC SYNTHESIS, P1, DOI 10.1002/3527604677

[6] Prins cyclizations in silyl additives with suppression of epimerization: Versatile tool in the synthesis of the tetrahydropyran backbone of natural products [J].

Chan, KP ;

Loh, TP .

ORGANIC LETTERS, 2005, 7 (20) :4491-4494

[7]

Christmann M, 2000, ANGEW CHEM INT EDIT, V39, P4364, DOI 10.1002/1521-3773(20001201)39:23<4364::AID-ANIE4364>3.0.CO

[8]

2-G

[9] LAULIMALIDES - NEW POTENT CYTO-TOXIC MACROLIDES FROM A MARINE SPONGE AND A NUDIBRANCH PREDATOR [J].

CORLEY, DG ;

HERB, R ;

MOORE, RE ;

SCHEUER, PJ ;

PAUL, VJ .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (15) :3644-3646

[10]

Dalko P.I., 2007, ENANTIOSELECTIVE ORG

← 1 2 3 4 5 6 7 →