ChemInform Abstract: Design of a New Chiral Host Compound, trans‐4,5‐Bis(hydroxydiphenylmethyl)‐2,2‐dimethyl‐1,3‐dioxacyclopentane. An Effective Optical Resolution of Bicyclic Enones Through Host‐Guest Complex Formation.

Abstract

Diethyl tartrate (I) is converted to the bis(diarylhydroxymethyl)dioxoles (V) by consecutive reaction with the dimethoxypropane (II) and the Grignard compounds (IV).

New technique in optical resolutions

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Optical resolutions by inclusion complexation with a chiral host compound

“…7 The same treatments of 83a-c, 84, and 85 with 8a gave optically pure (-)-83a (41%), (-)-83b (62%), (-)-83c (43%), (+)-84 (80%), and (-)-85 (58%), respectively, in the yields indicated. n 7 Mechanism of these precise chiral recognitions between 8 and bicyclic ketones have been clarified by X-ray study of two inclusion complexes of 8a with (-)-83b and with (-)-86. 35 In the optical resolution of bicyclo[2.…”

“…(R,R)-(+)-trans-4,5-bis(hydroxydiphenylmethyl)-2,3-dimethyl-1,3-dioxacyclopentan e (8a) was prepared by the reaction with PhMgBr of the acetal (7) derived from diethyl tartarate (6) and acetone. 7 By the same method, 9 and 10 were also prepared. 8 Some amide derivatives have been reported to form inclusion complex with a wide variety of organic compounds.…”