Synthesis and molecular structure of belted spirocyclic tetrahydrofurans, a new class of preorganized hosts for cations

LA Paquette, JT Negri, RD Rogers

Index: Paquette, Leo A.; Negri, Joanna T.; Rogers, Robin D. Journal of Organic Chemistry, 1992 , vol. 57, # 14 p. 3947 - 3956

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Citation Number: 54

Abstract

The preparation and binding properties of spirocyclic tetrahydrofurans 7-1 1 are described. The condensation of cyclopentanone with 5-lithio-2, 3-dihydrofuran (12) provided an alcohol which readily rearranged to ketone 14 under acidic conditions." Capping" of the carbonyl group in 14 so as to generate a second spiro tetrahydrofuran subunit gave rise to 7 and 8. Starting with cyclobutanone, 2-fold ring expansion involving 12 provided the key reactions ...