Tetramethyl 1, 1, 4, 4-cyclohexanetetracarboxylate: preparation and conversion to key precursors of fluorinated, stereochemically defined cyclohexanes

CR Davis, DC Swenson, DJ Burton

Index: Davis, Charles R.; Swenson, Dale C.; Burton, Donald J. Journal of Organic Chemistry, 1993 , vol. 58, # 24 p. 6843 - 6850

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Citation Number: 22

Abstract

Stereoselective low-temperature diisobutylaluminum hydride (DIBALH) reduction of the title tetraester 3 affords trans-l, 4-dialdehyde 4a as the major product. Fluorination of 4a, b, followed by additional elaboration leads to novel, 1, 1, 4, 4-tetrasubstituted cyclohexanes bearing tram-1, 4-difluoromethyl and fluoromethyl groups. The effect of ring size and number of ester substituents on the outcome of the reduction has been examined and treatment of ...