Tetrahedron

Preliminary investigations on novel camphor-derived chiral sulfones: completely stereoselective formation of tricyclic β-hydroxy sulfones from 8-and 10-functionalized …

FW Lewis, TC McCabe, DH Grayson

Index: Lewis, Frank W.; McCabe, Thomas C.; Grayson, David H. Tetrahedron, 2011 , vol. 67, # 39 p. 7517 - 7528

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Citation Number: 8

Abstract

Some camphor-derived chiral allylic and benzylic sulfones in which the sulfonyl group is located at the C-10, C-9 or C-8 methyl groups of (+)-camphor were synthesized. The C-9 and C-8 substituted sulfones were obtained via Wagner–Meerwein rearrangements of the bicyclic camphor framework. On treatment with LDA, the C-10 and C-8 substituted sulfones cyclized with complete stereoselectivity, affording tricyclic β-hydroxy sulfones whose ...