Catalytic enantioselective alkene epoxidation using novel spirocyclic N-carbethoxy-azabicyclo[3.2.1]octanones

被引：10

作者：

Armstrong, Alan ^{[1
]}

Bettati, Michela ^{[1
]}

White, Andrew J. P. ^{[1
]}

机构：

[1] Univ London Imperial Coll Sci Technol & Med, Dept Chem, London SW7 2AZ, England

来源：

TETRAHEDRON | 2010年 / 66卷 / 33期

关键词：

Epoxidation; Asymmetric; Ketone; Dioxirane; PLANAR TRANSITION-STATES; ASYMMETRIC EPOXIDATION; CHIRAL DIOXIRANE; ORGANIC-SYNTHESIS; TERMINAL OLEFINS; KETONES; DERIVATIVES; OXIDATION; STYRENES; SPIRO;

D O I：

10.1016/j.tet.2010.04.004

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A general synthetic route allowing access to several spirocyclic N-carbethoxy-azabicyclo[3.2.1]octanones is developed. These novel ketones efficiently catalyse alkene epoxidation using Oxone (R) with up to 91.5% ee. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：6309 / 6320

页数：12

共 32 条

[1] A new class of chiral tetrahydropyran-4-one catalyst for asymmetric epoxidation of alkenes [J].

Armstrong, A ;

Tsuchiya, T .

TETRAHEDRON, 2006, 62 (2-3) :257-263

[2] Enantioselective epoxidation of alkenes catalyzed by 2-fluoro-N-carbethoxytropinone and related tropinone derivatives [J].

Armstrong, A ;

Ahmed, G ;

Dominguez-Fernandez, B ;

Hayter, BR ;

Wailes, JS .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (24) :8610-8617

[3] Asymmetric epoxidation catalyzed by esters of α-hydroxy-8-oxabicyclo[3.2.1]octan-3-one [J].

Armstrong, A ;

Moss, WO ;

Reeves, JR .

TETRAHEDRON-ASYMMETRY, 2001, 12 (20) :2779-2781

[4] Catalytic enantioselective epoxidation of alkenes with a tropinone-derived chiral ketone [J].

Armstrong, A ;

Hayter, BR .

CHEMICAL COMMUNICATIONS, 1998, (05) :621-622

[5] α-functionalised ketones as promoters of alkene epoxidation by Oxone® [J].

Armstrong, A ;

Hayter, BR .

TETRAHEDRON, 1999, 55 (36) :11119-11126

[6] Alkene epoxidation catalyzed by bicyclo[3.2.1]octan-3-ones: effects of structural modifications on catalyst efficiency and epoxidation enantioselectivity [J].

Armstrong, A ;

Hayter, BR ;

Moss, WO ;

Reeves, JR ;

Wailes, JS .

TETRAHEDRON-ASYMMETRY, 2000, 11 (10) :2057-2061

[7] Bicyclo[3.2.1]octanone catalysts for asymmetric alkene epoxidation: the effect of disubstitution [J].

Armstrong, Alan ;

Dominguez-Fernandez, Belen ;

Tsuchiya, Tomoki .

TETRAHEDRON, 2006, 62 (28) :6614-6620

[8] STEREOSELECTIVE SYNTHESIS OF 2,4,6-TRIMETHYLCYCLOHEX-4-ENE-1,3-DIOL DERIVATIVES AND OF POLYPROPIONATE FRAGMENTS WITH 4 CONTIGUOUS STEREOGENIC CENTERS [J].

BIALECKI, M ;

VOGEL, P .

HELVETICA CHIMICA ACTA, 1995, 78 (02) :325-343

[9] Accessible sugars as asymmetric olefin epoxidation organocatalysts: glucosaminide ketones in the synthesis of terminal epoxides [J].

Boutureira, Omar ;

McGouran, Joanna F. ;

Stafford, Robert L. ;

Emmerson, Daniel P. G. ;

Davis, Benjamin G. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2009, 7 (20) :4285-4288

[10] Enantioselective Epoxidation of Nonconjugated cis-Olefins by Chiral Dioxirane [J].

Burke, Christopher P. ;

Shi, Yian .

ORGANIC LETTERS, 2009, 11 (22) :5150-5153

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