Diastereoselective synthesis of 4,5-dihydrofurans by iodoenolcyclisation of 2-allyl-1,3-dicarbonyl compounds

被引：30

作者：

Antonioletti, R ^{[1
]}

Malancona, S ^{[1
]}

Bovicelli, P ^{[1
]}

机构：

[1] Univ Roma La Sapienza, CNR, Inst Chim Biomol, Sez Roma,Dipartimento Chim, I-00185 Rome, Italy

来源：

TETRAHEDRON | 2002年 / 58卷 / 43期

关键词：

cyclisation; furans; enols and derivatives;

D O I：

10.1016/S0040-4020(02)01064-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A study of the stereochemical aspects of I-2-induced cyclisation of 2-alkenyl-1,3-dicarbonyl compounds reveals that the iodoenolcyclisation is strictly dependent on the dicarbonyl species and the substituents in the allylic position. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：8825 / 8831

页数：7

共 43 条

[1] A new route to 2-alkenyl-1,3-dicarbonyl compounds, intermediates in the synthesis of dihydrofurans [J].

Antonioletti, R ;

Bovicelli, P ;

Malancona, S .

TETRAHEDRON, 2002, 58 (03) :589-596

[2] A CONVENIENT APPROACH TO FURAN-DERIVATIVES BY I-2-INDUCED CYCLIZATION OF 2-ALKENYL SUBSTITUTED 1,3-DICARBONYL COMPOUNDS [J].

ANTONIOLETTI, R ;

BONADIES, F ;

SCETTRI, A .

TETRAHEDRON LETTERS, 1988, 29 (39) :4987-4990

[3] New dihydrofuran and dihydropyran derivatives by iodoenolcyclization of 2-prenyl-1,3-dicarbonyl compounds: Studies on the regiochemistry [J].

Antonioletti, R ;

D'Onofrio, F ;

Rossi, B .

SYNTHETIC COMMUNICATIONS, 2001, 31 (06) :911-918

[4] IODOENOLCYCLIZATION .3. A GENERAL-APPROACH TO TETRASUBSTITUTED FURANS FROM 2-ALKENYL-1,3-DICARBONYL COMPOUNDS [J].

ANTONIOLETTI, R ;

CECCHINI, C ;

CIANI, B ;

MAGNANTI, S .

TETRAHEDRON LETTERS, 1995, 36 (49) :9019-9022

[5]

ANTONIOLETTI R, 1994, TETRAHEDRON LETT, V35, P4987

[6] RULES FOR RING-CLOSURE [J].

BALDWIN, JE .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1976, (18) :734-736

[7]

Bartlett P.A., 1984, ASYMMETRIC SYNTHESIS, V3, P411

[8] ELECTROPHILIC LACTONIZATION AS A TOOL IN ACYCLIC STEREOCONTROL - SYNTHESIS OF SERRICORNIN [J].

BARTLETT, PA ;

RICHARDSON, DP ;

MYERSON, J .

TETRAHEDRON, 1984, 40 (12) :2317-2327

[9]

BARTLETT PA, 1980, TETRAHEDRON, V36, P2

[10]

BIRD CW, 1984, COMPREHENSIVE HETERO, V4, P3

← 1 2 3 4 5 →