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A highly enantioselective synthesis of (R)- and (S)-5,7-odimethyleucomol
Journal article   Peer reviewed

A highly enantioselective synthesis of (R)- and (S)-5,7-odimethyleucomol

Franklin A. Davis and Bang-Chi Chen
Tetrahedron letters, v 31(47), pp 6823-6826
1990

Abstract

Both (R)- and (S)-5,7-O-dimethyleucomol 1b (R = Me) were synthesized in 57% overall yield in >96% enantiomeric excess. The key step involves the enantioselective α hydroxylation of the lithium enolate of 8 by readily available (+)- and (−)-[(8,8-dimethoxycamphoryl)sulfonyl]oxaziridine 9c. Both (R)- and (S)-5,7-O-dimethyleucomol 1b were synthesized in 57% overall yield in >96% ee via the enantioselective α-hydroxylation of the lithium enolate of 8 by (+)- and (−)- 9c.

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Chemistry, Organic
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