Transition-metal-mediated dihydropyran syntheses.: Exo selective hetero Diels-Alder reactions of colbaloxime dienyl complexes with aldehydes

被引：16

作者：

Adams, TA ^{[1
]}

Welker, ME ^{[1
]}

Day, CS ^{[1
]}

机构：

[1] Wake Forest Univ, Dept Chem, Winston Salem, NC 27109 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1998年 / 63卷 / 11期

关键词：

D O I：

10.1021/jo980077u

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cobaloxime 1,3-dienyl complex, 2-pyridine bis(dimethylglyoximato)cobalt(III)-(3E)-1,3-pentadiene, participates in exo selective hetero Diels-Alder reactions with a variety of alkyl and aryl aldehydes. The cobaloxime-substituted cycloadduct products of these reactions can be demetalated to provide diastereomerically pure dihydropyrans with concomitant cobalt recovery. One of the cobaloxime-substituted dihydropyrans has been characterized by X-ray crystallography to prove the exo selective nature of the Diels-Alder cycloaddition.

引用

页码：3683 / 3686

页数：4

共 28 条

[1] Synthesis of cobaloxime-substituted alpha,beta-unsaturated acyl complexes via reactions of cobaloxime anions and/or hydrides with ynones, ynoates, and alpha,beta-unsaturated acyl electrophiles [J].

Adams, TA ;

Welker, ME ;

LiableSands, LM ;

Rheingold, AL .

ORGANOMETALLICS, 1997, 16 (06) :1300-1307

[2] EXOSELECTIVE DIELS-ALDER REACTIONS OF AMINOCARBENE COMPLEXES [J].

ANDERSON, BA ;

WULFF, WD ;

POWERS, TS ;

TRIBBITT, S ;

RHEINGOLD, AL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (27) :10784-10798

[3] ASYMMETRIC EXO-SELECTIVE DIELS-ALDER REACTIONS OF CYCLIC BF2 ADDUCTS OF FUNCTIONALIZED FISCHER VINYLCARBENE COMPLEXES WITH CHIRAL 2-AMINO-1,3-DIENES [J].

BARLUENGA, J ;

CANTELI, RM ;

FLOREZ, J ;

GARCIAGRANDA, S ;

GUTIERREZRODRIGUEZ, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (15) :6949-6950

[4]

Bulkowski J., 1980, INORG SYNTH, V20, P127

[5] Preparation of (L)(N,N'-ethylenebis(salicylideneaminato))-(1,3-butadien-2-yl)cobalt(III) complexes and their utilization in facile and regioselective Diels-Alder reactions [J].

Chapman, JJ ;

Welker, ME .

ORGANOMETALLICS, 1997, 16 (04) :747-755

[6] A NEW APPROACH TO THE SYNTHESIS OF HEXOSES - AN ENTRY TO (+/-)-FUCOSE AND (+)-DAUNOSAMINE [J].

DANISHEFSKY, SJ ;

MARING, CJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (05) :1269-1274

[7] ON THE SCOPE, MECHANISM, AND STEREOCHEMISTRY OF THE LEWIS ACID-CATALYZED CYCLOCONDENSATION OF ACTIVATED DIENES WITH ALDEHYDES - AN APPLICATION TO THE ERYTHRONOLIDE PROBLEM [J].

DANISHEFSKY, SJ ;

LARSON, E ;

ASKIN, D ;

KATO, N .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (05) :1246-1255

[8] TOTAL SYNTHESIS OF VINEOMYCINONE-B2 METHYL-ESTER [J].

DANISHEFSKY, SJ ;

UANG, BJ ;

QUALLICH, G .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (05) :1285-1293

[9] CHELATION-CONTROLLED FACIALLY SELECTIVE CYCLOCONDENSATION REACTIONS OF CHIRAL ALKOXY ALDEHYDES - SYNTHESES OF A MOUSE ANDROGEN AND OF A CARBON-LINKED DISACCHARIDE [J].

DANISHEFSKY, SJ ;

PEARSON, WH ;

HARVEY, DF ;

MARING, CJ ;

SPRINGER, JP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (05) :1256-1268

[10] EXO-SELECTIVE DIELS-ALDER REACTIONS OF ALPHA,BETA-UNSATURATED HEXACARBONYL DIIRON BRIDGING ACYL COMPLEXES [J].

GILBERTSON, SR ;

ZHAO, XD ;

DAWSON, DP ;

MARSHALL, KL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (18) :8517-8518

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