Carbohydrate chemistry hetero Diels-Alder reactions

Y. Chapleur and M.-N. Euvrard, Hetero Diels-Alder reactions in carbohydrate chemistry A new strategy for multichiral arrays synthesis, J. Chem. Soc. Chem. Commun. p. 884 (1987). 

Osborn, H. M. I., Coisson, D. Application of the asymmetric hetero diels-alder reaction for synthesising carbohydrate derivatives and glycosidase inhibitors. Mini-Reviews in Organic Chemistry 200i, 1,41-54. 

Although carbohydrates are cheap and readily available chiral compounds, their application in stereoselective synthesis was for a long time limited to ex-chiral-pool syntheses [3]. They have been considered too complex compared to other chiral auxiliaries, for example a-pinene in borane-chemistry [4] or BINAP-derivatives in reduction chemistry [5]. However, it has been shown during the past few years that carbohydrates can be successfully applied as stereodifferentiating tools in many different reaction types such as aldol- [6], hydrogenation- [7], carbonyl addition- [8], Michael- [9], Diels-Alder- [10], hetero-Diels-Alder [11], and rearrangement reactions [12]. 

A review of cycloaddition reactions in carbohydrate chemistry is presented. The use of carbohydrate-derived dienes and dienophiles in the Diels-Alder reaction, hetero-Diels-Alder and dipolar addition reactions of carbohydrates are described. Stereochemical aspects of the cycloaddition processes are also discussed, and applications to the synthesis of natural products are included for each reaction type. Much of the material presented has appeared in the literature within the past five years however, earlier studies are also included in order to give a more representative historical perspective. 

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