Tetrahedron

Asymmetric spirocyclization: A new type of acid-catalyzed intramolecular 1, 4-addition to form carba-spirocyclic compounds

…, S Karasawa, Y Takahashi, M Aso, H Suemune

Index: Yamada, Satoshi; Karasawa, Satoru; Takahashi, Youichi; Aso, Mariko; Suemune, Hiroshi Tetrahedron, 1998 , vol. 54, # 51 p. 15555 - 15566

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Citation Number: 16

Abstract

Novel spirocyclization based on intramolecular 1, 4-addition and its asymmetric version have been developed using a combination of Lewis acid and 1, 2-diol. Treatment of five-and six-membered α, β-unsaturated cyclic ketones having a 4-oxopentyl group at the β-position with Lewis acid and ethylene glycol gave spiro [4.5] decane-2, 7-dione and spiro [5.5] undecane-2, 8-dione, respectively. The asymmetric version of this reaction has been ...