Diels asymmetric

Catalytic asymmetric hetero-Diels-Alder addition of carbonyl compounds 99ACR605. 

Metal-catalyzed asymmetric hetero Diels-Alder reactions of unactivated dienes with glyoxylates 98PAC1117. 

Catalytic asymmetric Diels-Alder reactions are presented by Hayashi, who takes as the starting point the synthetically useful breakthrough in 1979 by Koga et al. The various chiral Lewis acids which can catalyze the reaction of different dieno-philes are presented. Closely related to the Diels-Alder reaction is the [3-1-2] carbo-cyclic cycloaddition of palladium trimethylenemethane with alkenes, discovered by Trost and Chan. In the second chapter Chan provides some brief background information about this class of cycloaddition reaction, but concentrates primarily on recent advances. The part of the book dealing with carbo-cycloaddition reactions is... 

Asymmetric Diels-Alder reactions using a dienophile containing a chiral auxiliary were developed more than 20 years ago. Although the auxiliary-based Diels-Alder reaction is still important, it has two drawbacks - additional steps are necessary, first to introduce the chiral auxiliary into the starting material, and then to remove it after the reaction. At least an equimolar amount of the chiral auxiliary is, moreover, necessary. After the discovery that Lewis acids catalyze the Diels-Alder reaction, the introduction of chirality into such catalysts has been investigated. The Diels-Alder reaction utilizing a chiral Lewis acid is truly a practical synthetic transformation, not only because the products obtained are synthetically useful, but also because a catalytic amount of the chiral component can, in theory, produce a huge amount of the chiral product. 

The Asymmetric Diels-AIder Reaction of a,jS-Unsaturated Aldehydes as Dienophiles 1.2.1.1 Aluminum... 

Table 1.1 Asymmetric Diels-Alder reactions of cyclopentadiene catalyzed by CAB catalyst 3 [5a,b ...

The polymer-supported chiral oxazaborolidinone catalyst 5 prepared from valine was found by Ituno and coworkers to be a practical catalyst of the asymmetric Diels-Alder reaction [7] (Scheme 1.12). Of the several cross-linked polymers with a... 

Table 1.3 Asymmetric Diels-Alder reactions of a-substituted aldehydes catalyzed by 7 [10a,d ...

Table 1.5 Asymmetric Diels-Alder reactions catalyzed by 8 [10d ...

Table 1.8 Asymmetric Diels-Alder reactions of alkynyl aldehydes catalyzed by 9 [12 ...

Kanemasa et al. discovered an asymmetric Diels-Alder reaction of acryloyl-oxazolidi-none and cyclopentadiene catalyzed by a chiral aqua complex of 4,6-dibenzofurani-dyl-2,2 -bis(4-phenyloxazoline) 16 (vide infra) [22]. Unlike the Diels-Alder reaction of acryloyloxazolidinone, for which NiBr2/AgC104 and Znl2/AgC104 are the most suitable sources of the central metal, the best for the Diels-Alder reaction of a-bromo-... 

The Asymmetric Diels-Alder Reaction of a,/ -Unsaturated Esters as Dienophiles... 

I 1 Catalytic Asymmetric Diels-Alder Reactions 1.2.3.1 Aluminum... 

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