BIFUNCTIONALIZED ALLENES. PART. X. AN ELECTROPHILIC CYCLIZATION PROTOCOL FOR CONVENIENT HIGHLY REGIOSELECTIVE SYNTHESIS OF 3-SULFONYLFURAN-2(5H)-ONES FROM 2-SULFONYLALLENOATES

被引：10

作者：

Christov, Valerij Ch ^{[1
]}

Ivanov, Ivaylo K. ^{[1
]}

Ismailov, Ismail E. ^{[1
]}

机构：

[1] Konstantin Preslavsky Univ Shumen, Fac Nat Sci, Dept Organ Chem & Technol, BG-9712 Shumen, Bulgaria

来源：

HETEROCYCLES | 2013年 / 87卷 / 09期

关键词：

2-Sulfonylallenecarboxylate; 3-Sulfonylfuran-2(5H)-one; Neighbouring Group Participation; 2-Sulfonylalka-2,3-, and-2,4-dien-1-ones; ALPHA; BETA-UNSATURATED GAMMA-SULTINES; 1-SUBSTITUTED PHOSPHORYLATED ALLENES; ONE-POT SYNTHESIS; 2,3-ALLENOIC ACIDS; FRAGMENTATION-CYCLIZATION; STEREOSELECTIVE-SYNTHESIS; SUBSTITUTED BUTENOLIDES; BETA-HALOBUTENOLIDES; ASYMMETRIC-SYNTHESIS; NATURAL-PRODUCTS;

D O I：

10.3987/COM-13-12769

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple and convenient protocol for the highly regioselective synthesis of 3-sulfonylfuran-2(5H)-ones by electrophilic cyclization reaction of 2-sulfonylallenecarboxylates with neighbouring ester group participation is described. However, the reaction of 2-sulfonylalka-2,3-dien-1-ones with electrophilic reagents proceeded with formation of 2-sulfonylalka-2,4-dien-1-ones by addition-elimination reaction. A possible mechanism involving the cyclization and addition-elimination reaction of 2-sulfonyl-substituted allenic esters and ketones was proposed.

引用

页码：1903 / 1916

页数：14

共 60 条

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