The Synthesis of a Chiral Hexaphenyl-18-crown-6 Derivative

John Crosby; J. Fraser Stoddart; Xiaoqiang Sun; Mark R. W. Venner

doi:10.1055/s-1993-25818

Synthesis 1993; 1993(1): 141-145
DOI: 10.1055/s-1993-25818

paper

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The Synthesis of a Chiral Hexaphenyl-18-crown-6 Derivative

John Crosby^* , J. Fraser Stoddart, Xiaoqiang Sun, Mark R. W. Venner

^*ICI FCMO, Hexagon House, Blackley, Manchester M9 3DA, England

Abstract

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The stereospecific synthesis of (2R,3R,8R,9R,14R,15R)-2, 3,8,9,14,15-hexaphenyl-1,4,7,10,13,16-hexaoxacyclooctadedecane [(R,R,R,R,R,R)-12] from (R,R)-hydrobenzoin [(R,R)-1] is reported. The ability of (R,R,R,R,R,R)-12 to act as a chiral solid-liquid phase-transfer catalyst in an asymmetric Michael addition is compared with the efficiencies of other chiral di- and tetra-substituted 18-crown-6 derivatives, both with respect to product conversions and chirality transfers from catalysts to products.

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