Lewis acid-catalyzed tandem Diels-Alder reaction/retro-claisen rearrangement as an equivalent of the inverse electron demand hetero Diels-Alder reaction

被引：32

作者：

Davies, HML ^{[1
]}

Dai, X ^{[1
]}

机构：

[1] SUNY Buffalo, Dept Chem, Buffalo, NY 14260 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 70卷 / 17期

关键词：

D O I：

10.1021/jo050821s

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A highly stereoselective formal inverse electron demand hetero Diels-Alder reaction (HDA) occurs on reaction of 2-aryl-a,beta-unsaturated aldehydes with cyclopentadiene. The major pathway for this transformation is shown to be a Lewis acid-catalyzed tandem Diels-Alder reaction/retro-Claisen rearrangement.

引用

收藏

页码：6680 / 6684

页数：5

相关论文

共 42 条

[1] STRUCTURE OF MONENSIC ACID A NEW BIOLOGICALLY ACTIVE COMPOUND [J].

AGTARAP, A ;

CHAMBERLIN, JW ;

PINKERTON, M ;

STEINRAUF, L .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (22) :5737-+

[2]

[Anonymous], 1991, Comprehensive Organic Synthesis

[3] The first synthesis of phosphonoacrolein. Application to Diels-Alder reaction as heterodiene [J].

Arimori, S ;

Kouno, R ;

Okauchi, T ;

Minami, T .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (21) :7303-7308

[4] A novel catalytic and highly enantioselective approach for the synthesis of optically active carbohydrate derivatives [J].

Audrain, H ;

Thorhauge, J ;

Hazell, RG ;

Jorgensen, KA .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (15) :4487-4497

[5] SYNTHETIC AND MECHANISTIC STUDIES OF THE RETRO-CLAISEN REARRANGEMENT - AN EXAMPLE OF CATION ACCELERATION OF A (3,3)-SIGMATROPIC REARRANGEMENT [J].

BOECKMAN, RK ;

FLANN, CJ ;

POSS, KM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (14) :4359-4362

[6]

Boger D. L., 1987, HETERO DIELS ALDER M

[7] THE STRUCTURE AND ABSOLUTE STEREOCHEMISTRY OF ZINCOPHORIN (ANTIBIOTIC M144255) - A MONOBASIC CARBOXYLIC-ACID IONOPHORE HAVING A REMARKABLE SPECIFICITY FOR DIVALENT-CATIONS [J].

BROOKS, HA ;

GARDNER, D ;

POYSER, JP ;

KING, TJ .

JOURNAL OF ANTIBIOTICS, 1984, 37 (11) :1501-1504

[8] STEREOCHEMISTRY OF PALYTOXIN .4. COMPLETE STRUCTURE [J].

CHA, JK ;

CHRIST, WJ ;

FINAN, JM ;

FUJIOKA, H ;

KISHI, Y ;

KLEIN, LL ;

KO, SS ;

LEDER, J ;

MCWHORTER, WW ;

PFAFF, KP ;

YONAGA, M ;

UEMURA, D ;

HIRATA, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (25) :7369-7371

[9] Catalyst-controlled inverse-electron-demand hetero-Diels-Alder reactions in the enantio- and diastereloselective synthesis of iridoid natural products [J].

Chavez, DE ;

Jacobsen, EN .

ORGANIC LETTERS, 2003, 5 (14) :2563-2565

[10] TOTAL SYNTHESIS OF GIBBERELLIC-ACID - A SIMPLE SYNTHESIS OF A KEY INTERMEDIATE [J].

COREY, EJ ;

MUNROE, JE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (22) :6129-6130

← 1 2 3 4 5 →