The Journal of Organic Chemistry

A new variant of the Claisen rearrangement capable of creating the bond between two quaternary centers

AA Ponaras

Index: Ponaras, A. A. Journal of Organic Chemistry, 1983 , vol. 48, # 21 p. 3866 - 3868

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Citation Number: 62

Abstract

2a,b 30,b or=4 o n=3 (1) ... 20 t 2a.b RCHO L', TES3 &ZCl2 ) RCTBS ( 2 ) H 2 @,b 2 0 ... 7 a,b 8a,b 8 R=$ b R=Et single diastereomer is obtained. While the axial disposition of the methine protons in 8a and 8b could be established by NMR methods, the actual assignment of relative con- figurations relies on precedent.4b With an eventual aim toward the avermectins, other formats for spirocyclization were examined. Reduction of 7a with DIBAH gave an 8690 yield of ...