Transacetalization of Diethyl Tartrate with Acetals of. alpha.-Dicarbonyl Compounds: A Simple Access to a New Class of C2-Symmetric Auxiliaries and Ligands

U Berens, D Leckel, SC Oepen

Index: Berens, Ulrich; Leckel, Dieter; Oepen, Susanne C. Journal of Organic Chemistry, 1995 , vol. 60, # 25 p. 8204 - 8208

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Citation Number: 64

Abstract

18 19 with 1 equiv of 3 in the presence of BF3-etherateloa afforded a mixture of diastereomeric 1, Cdioxanes in a ratio of ca. 80: 15: 5. The structural assignment of the main diastereomer 8 is based on its 'H-NMR, which reveals a C2-symmetry and from the chemical shiR of the methoxy groups in the derivative 21 (vide infra). Obviously, transacetalizations of 1 with 2 or 3 are closely related to the formation of acetals from 1, 2-diols and the “Dispoke ...