A novel and facile one-pot sulfonyloxylactonization of alkenoic acids

被引：1

作者：

Zhu, Min ^{[1
]}

Ll, Li ^{[1
]}

Liu, Cai Qin ^{[1
]}

机构：

[1] Zhejiang Shuren Univ, Coll Biol & Environm Sci, Hangzhou 310015, Zhejiang, Peoples R China

来源：

CHINESE CHEMICAL LETTERS | 2009年 / 20卷 / 12期

基金：

美国国家科学基金会;

关键词：

Sulfonyloxylactonization; (Diacetoxyiodo)benzene; Alkenoic acid; Synthesis; POLYVALENT IODINE COMPOUNDS; HYPERVALENT IODINE; CYCLIZATION; KETONES; SALTS;

D O I：

10.1016/j.cclet.2009.06.015

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The novel and facile one-pot method for sulfonyloxylactonization of alkenoic acids was reported: when (diacetoxyiodo)benzene, various 4-pentenoic acids or 5-hexenoic acid and sulfonic acids were mixed in CH2Cl2 at room temperature, sulfonyloxylactons were obtained in good to excellent yields in short times, some had two diastereoisomers. (C) 2009 Min Zhu. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

引用

页码：1427 / 1430

页数：4

共 22 条

[1] STEREOSELECTIVE EPOXIDATION OF ACYCLIC OLEFINIC CARBOXYLIC-ACIDS VIA IODO-LACTONIZATION
BARTLETT, PA
MYERSON, J
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (12) : 3950 - 3952
[2] SYNTHESIS AND SYNTHETIC UTILITY OF HALOLACTONES
DOWLE, MD
DAVIES, DI
[J]. CHEMICAL SOCIETY REVIEWS, 1979, 8 (02) : 171 - 197
[3] Cyclic diaryliodonium ions: old mysteries solved and new applications envisaged
Grushin, VV
[J]. CHEMICAL SOCIETY REVIEWS, 2000, 29 (05) : 315 - 324
[4] Reagent-controlled stereoselective iodolactonizations
Haas, J
Piguel, S
Wirth, T
[J]. ORGANIC LETTERS, 2002, 4 (02) : 297 - 300
[5] Harding K.E., 1991, COMPREHENSIVE ORGANI, V4, P363
[6] PREPARATION OF [HYDROXY(((+)-10-CAMPHORSULFONYL)OXY)IODO]BENZENE AND ITS REACTIVITY TOWARD CARBONYL-COMPOUNDS
HATZIGRIGORIOU, E
VARVOGLIS, A
BAKOLACHRISTIANOPOULOU, M
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (01) : 315 - 318
[7] Regioselective synthesis of 6-prenylpolyhydroxyisoflavone (wighteone) and wighteone hydrate with hypervalent iodine
Hossain, MM
Tokuoka, T
Yamashita, K
Kawamura, Y
Tsukayama, M
[J]. SYNTHETIC COMMUNICATIONS, 2006, 36 (09) : 1201 - 1211
[8] A novel one-pot synthesis of 3-carbomethoxy-4-arylfuran-2-(5H)-ones from ketones using [hydroxy(tosyloxy)iodo]benzene
Karade, Nandkishor N.
Gampawar, Sumeet V.
Kondre, Jeevan M.
Shinde, Sandeep V.
[J]. TETRAHEDRON LETTERS, 2008, 49 (28) : 4402 - 4404
[9] Kirschning A, 1998, EUR J ORG CHEM, V1998, P2267
[10] DIRECT ALPHA-PHOSPHORYLOXYLATION OF KETONES AND PHOSPHORYLOXYLACTONIZATION OF PENTENOIC ACIDS WITH [HYDROXY((BIS(PHENYLOXY)PHOSPHORYL)OXY)IODO]BENZENE
KOSER, GF
LODAYA, JS
RAY, DG
KOKIL, PB
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (09) : 2987 - 2988

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