Studies on novel synthetic methodologies, part 66. Organic reactions in water: an efficient one-pot synthesis of acyloxiranes from Baylis-Hillman adducts using hypervalent iodine

被引：22

作者：

Das, B ^{[1
]}

Holla, H ^{[1
]}

Venkateswarlu, K ^{[1
]}

Majhi, A ^{[1
]}

机构：

[1] Indian Inst Chem Technol, Organ Chem Div 1, Hyderabad 500007, Andhra Pradesh, India

来源：

TETRAHEDRON LETTERS | 2005年 / 46卷 / 51期

关键词：

Baylis-Hillman adducts; hypervalent iodine; PhI=O; acyloxiranes; aqueous medium;

D O I：

10.1016/j.tetlet.2005.10.078

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Treatment of Baylis-Hillman adducts with iodosobenzene (PhI=O) in the presence of a catalytic amount of KBr in water at room temperature afforded the corresponding acyloxiranes in good yields. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：8895 / 8897

页数：3

共 14 条

[1] A new protocol for the syntheses of (E)-3-benzylidenechroman-4-ones:: a simple synthesis of the methyl ether of bonducellin [J].

Basavaiah, D ;

Bakthadoss, M ;

Pandiaraju, S .

CHEMICAL COMMUNICATIONS, 1998, (16) :1639-1640

[2] A convenient method for the preparation of benzopyrano- and furopyrano-2-isoxazoline derivatives using hypervalent iodine reagents [J].

Das, B ;

Holla, H ;

Mahender, G ;

Venkateswarlu, K ;

Bandgar, BP .

SYNTHESIS-STUTTGART, 2005, (10) :1572-1574

[3] An efficient stereoselective synthesis of (E)- and (Z)-trisubstituted alkenes from unactivated Baylis-Hillman adducts using NaBH4/CuCl2•2H2O [J].

Das, B ;

Banerjee, J ;

Majhi, A ;

Mahender, G .

TETRAHEDRON LETTERS, 2004, 45 (50) :9225-9227

[4] Hypervalent iodine-mediated interaction of aldoximes with activated alkenes including Baylis-Hillman adducts: a new and efficient method for the preparation of nitrile oxides from aldoximes [J].

Das, B ;

Holla, H ;

Mahender, G ;

Banerjee, J ;

Reddy, MR .

TETRAHEDRON LETTERS, 2004, 45 (39) :7347-7350

[5] A simple and facile stereoselective synthesis of (Z)- and (E)-allyl halides catalyzed by silica supported sodium hydrogen sulfate:: factors influencing the yields and stereochemistry of allyl halides [J].

Das, B ;

Banerjee, J ;

Ravindranath, N .

TETRAHEDRON, 2004, 60 (38) :8357-8361

[6] Organic reactions in water:: An efficient zinc-mediated stereoselective synthesis of (E)- and (Z)-trisubstituted alkenes using unactivated alkyl halides [J].

Das, B ;

Banerjee, J ;

Mahender, G ;

Majhi, A .

ORGANIC LETTERS, 2004, 6 (19) :3349-3352

[7] Chemoselective deprotection of trityl ethers using silica-supported sodium hydrogen sulfate [J].

Das, B ;

Mahender, G ;

Kumar, VS ;

Chowdhury, N .

TETRAHEDRON LETTERS, 2004, 45 (36) :6709-6711

[8]

FOUCAUD A, 1990, SYNTHESIS-STUTTGART, P787

[9] SYNTHESIS AND BIOLOGICAL-ACTIVITY OF ALPHA-METHYLENE-GAMMA-BUTYROLACTONES [J].

HOFFMANN, HMR ;

RABE, J .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1985, 24 (02) :94-110

[10]

HOHMA H, 2000, ANGEW CHEM INT EDIT, V39, P1306

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