Organocatalytic asymmetric Michael addition of 2,2-dimethyl-1,3-dioxan-5-one to nitro alkenes employing proline-based catalysts

被引：55

作者：

Enders, Dieter ^{[1
]}

Chow, Sharon ^{[1
]}

机构：

[1] Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2006年 / 2006卷 / 20期

关键词：

asymmetric synthesis; Michael addition; organocatalysis; dioxanone; nitro alkenes; proline-based catalysts;

D O I：

10.1002/ejoc.200600464

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The organocatalytic asymmetric Michael addition of 2,2-dimethyl-1,3-dioxiin-5-one (1) was performed with various nitro alkenes 2 using a number of proline-based catalysts (AM) affording polyfunctional nitro ketones 3. Reverse diastereoselectivity was observed with the diphenylprolinol catalyst J, and the best diastereo- and enantiomeric excesses were achieved with the sulfonamide catalyst M (de = 84-98%, ee = 81-86%). ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006).

引用

页码：4578 / 4584

页数：7

共 61 条

[1] Diamine-catalyzed asymmetric Michael additions of aldehydes and ketones to nitrostyrene [J].

Alexakis, A ;

Andrey, O .

ORGANIC LETTERS, 2002, 4 (21) :3611-3614

[2] The use of N-alkyl-2,2′-bipyrrolidine derivatives as organocatalysts for the asymmetric Michael addition of ketones and aldehydes to nitroolefins [J].

Andrey, O ;

Alexakis, A ;

Tomassini, A ;

Bernardinelli, G .

ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (9-10) :1147-1168

[3] Asymmetric Michael addition of α-hydroxyketones to nitroolefins catalyzed by chiral diamine [J].

Andrey, O ;

Alexakis, A ;

Bernardinelli, G .

ORGANIC LETTERS, 2003, 5 (14) :2559-2561

[4]

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

[5]

Berner OM, 2002, EUR J ORG CHEM, V2002, P1877

[6] Catalytic direct asymmetric Michael reactions: Addition of unmodified ketone and aldehyde donors to alkylidene malonates and nitro olefins [J].

Betancort, JM ;

Sakthivel, K ;

Thayumanavan, R ;

Tanaka, F ;

Barbas, CF .

SYNTHESIS-STUTTGART, 2004, (09) :1509-1521

[7] Catalytic direct asymmetric Michael reactions: Taming naked aldehyde donors [J].

Betancort, JM ;

Barbas, CF .

ORGANIC LETTERS, 2001, 3 (23) :3737-3740

[8] Catalytic enantioselective direct Michael additions of ketones to alkylidene malonates [J].

Betancort, JM ;

Sakthivel, K ;

Thayumanavan, R ;

Barbas, CF .

TETRAHEDRON LETTERS, 2001, 42 (27) :4441-4444

[9] 5-Pyrrolidin-2-yltetrazole as an asymmetric organocatalyst for the addition of ketones to nitro-olefins [J].

Cobb, AJA ;

Longbottom, DA ;

Shaw, DM ;

Ley, SV .

CHEMICAL COMMUNICATIONS, 2004, (16) :1808-1809

[10] HIGHLY ENANTIOSELECTIVE BORANE REDUCTION OF KETONES CATALYZED BY CHIRAL OXAZABOROLIDINES - MECHANISM AND SYNTHETIC IMPLICATIONS [J].

COREY, EJ ;

BAKSHI, RK ;

SHIBATA, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (18) :5551-5553

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