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Asymmetric induction through the use of remote covalent and ionic chiral auxiliaries in the solid state photochemistry of 2-benzoyladamantane-2-carboxylic acid derivatives

✍ Scribed by Eugene Cheung; Matthew R Netherton; John R Scheffer; James Trotter; Alla Zenova


Publisher
Elsevier Science
Year
2000
Tongue
French
Weight
87 KB
Volume
41
Category
Article
ISSN
0040-4039

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✦ Synopsis


Attachment of chiral auxiliaries to 2-benzoyladamantane-2-carboxylic acid, either covalently through ester formation with optically pure alcohols, or ionically via salt formation with optically pure amines, leads to substrates whose irradiation in the crystalline state affords chiral rearranged photoproducts in ]96% diastereo-and enantiomeric excess.