Carbohydrates as chiral auxiliary

Asymmetric syntheses of heterocycles using carbohydrates as chiral auxiliaries 97T14823. 

Nitroalkenes with Chiral Auxiliaries The use of carbohydrates as chiral auxiliary in Diels-Alder reactions for the stereoselective preparation of carbocyclic and heterocyclic chiral rings is well documented.48 For example, D-manno-nitroalkene reacts with 2,3-dimethyl-1,3-butadiene to give a 65 35 mixture of adducts, as shown in Eq. 8.29. The configurations at C-4 and C-5 have been determined to be (4R,5R) and (45,55), respectively. Hydrolysis of the product followed by degradative oxidation of the sugar side chains leads to enantiomerically... 

Mur 207), has received renewed interest in recent years. A fine review covering the intermolecular asymmetric Diels-Alder reaction was compiled by Mori 208>. In this article the use of terpenes and carbohydrates as chiral auxiliaries is discussed no amino acid derivatives are mentioned in this context. A chiral a-hydroxycarboxylic acid derivative was also used to achieve an asymmetric Diels-Alder reaction 209). High asymmetric induction could be detected in the intramolecular Diels-Alder reaction of chiral molecules. 

H. Kunz Stereoselective syntheses using carbohydrates as chiral auxiliaries G. W. Hart Ubiquitous and temporal glycosylation of nuclear and cytoplasmic proteins... 

Rueck, K, Kunz, H, Carbohydrates as chiral auxiliaries in stereoselective synthesis, Angew. Chem. Int. Ed., 32, 336-358, 1993. 

Charette, A B, Cote, B, Marcoux, J E, Carbohydrates as chiral auxiliaries asymmetric cyclopropanation reaction of acyclic olefins, J. Am. Chem. Soc., 113, 8166-8167, 1991. 

Kunz, H, Stereoselective syntheses using carbohydrates as chiral auxiliaries, Pure Appl. Chem., 67, 1627-1635, 1995. 

The use of carbohydrates as chiral auxiliaries in dienes has been described by Stoodley and co-workers (29). A series of glucopyranosyloxy-butadienes 57 wiA different diene substitution were synthesized and reacted with N-phenylmaleimide. 

While the evolved format of these Reports largely allows for the handling of new material, some adaptation is desirable and (after some debate) treatment of chain-extended sugar derivatives is now included in Chapter 2. Carbohydrates as chiral auxiliaries is another aspect that the normal format does not accommodate too readily it is treated in Chapter 24, and Chapter 4 now includes brief reference to chemical aspects of the cyclodextrins. 

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