An expedient stereoselective synthesis of (Z)- and (E)-ally iodides from Baylis-Hillman adducts along with selective iodination of benzylic alcohols using the polymethylhydrosiloxane-iodine system

被引：20

作者：

Das, Biswanath ^{[1
]}

Holla, Harish

Srinivas, Yallamalla

Chowdhury, Nikhil

Bandgar, B. P.

机构：

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

[2] Swami Ramanand Teerth Marathwada Univ, Sch Chem Sci, Organ Chem Res Lab, Vishnupuri 431606, Nanded, India

来源：

TETRAHEDRON LETTERS | 2007年 / 48卷 / 18期

关键词：

Baylis-Hillman adduct; (Z)- and (E)-Allyl iodides; polymethylhydrosiloxane (PMHS); iodine; benzylic iodide;

D O I：

10.1016/j.tetlet.2007.03.050

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A stereoselective method has been developed for the synthesis of (Z)- and (E)-allyl iodides from Baylis-Hillman adducts using polymethylhydrosiloxane (PMHS) and iodine in chloroform at room temperature. In addition, the reagent system has been utilized for the iodination of benzylic alcohols selectively. (c) 2007 Elsevier Ltd. All rights reserved.

引用

页码：3201 / 3204

页数：4

共 27 条

[1] NECIC ACID SYNTHONS .4. REGIOSELECTIVITY IN THE REACTIONS OF CHLORO AND IODO DERIVATIVES OF SELECTED 3-HYDROXY-2-METHYLENEALKANOATE ESTERS WITH ETHYL 2-METHYL-3-OXOBUTANOATE [J].

AMEER, F ;

DREWES, SE ;

HOUSTONMCMILLAN, MS ;

KAYE, PT .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (06) :1143-1145

[2] 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

[3] Recent advances in the Baylis-Hillman reaction and applications [J].

Basavaiah, D ;

Rao, AJ ;

Satyanarayana, T .

CHEMICAL REVIEWS, 2003, 103 (03) :811-891

[4]

Baylis A. B, DE Patent, Patent No. 2155113

[5] ALPHA-METHYLIDENE-BETA-LACTAMS AND ALPHA-ALKYLIDENE-BETA-LACTAMS FROM NONPROTEINOGENIC AMINO-ACIDS [J].

BUCHHOLZ, R ;

HOFFMANN, HMR .

HELVETICA CHIMICA ACTA, 1991, 74 (06) :1213-1220

[6] A facile and chemoselective conjugate reduction using polymethylhydrosiloxane (PMHS) and catalytic B(C6F5)3 [J].

Chandrasekhar, S ;

Chandrashekar, G ;

Reddy, MS ;

Srihari, P .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (09) :1650-1652

[7] Facile synthesis of 2Z-2-chloromethyl aryl-2-enoates [J].

Chavan, SP ;

Ethiraj, KS ;

Kamat, SK .

TETRAHEDRON LETTERS, 1997, 38 (42) :7415-7416

[8] Single-step stereoselective synthesis of (E)- and (Z)-allylamines from acetyl derivatives of Baylis-Hillman adducts [J].

Das, B ;

Mahender, G ;

Chowdhury, N ;

Banerjee, J .

SYNLETT, 2005, (06) :1000-1002

[9] 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

[10] 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

← 1 2 3 →