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Synthesis 1996; 1996(1): 116-122
DOI: 10.1055/s-1996-4169
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Synthesis of Chiral Hydroxylated Farnesene Derivatives

Margaret A. Brimble* , Daryl D. Rowan, Julie A. Spicer
  • *Department of Chemistry, University of Sydney, NSW 2006, Australia, Fax 61(2)3513329; E-mail: brimble_m@alf.chem.su.oz.au
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Publication History

Publication Date:
31 December 2000 (online)

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Asymmetric dihydroxylation of α-farnesene (4) using the ligand (DHQ)2-PHAL afforded predominantly (S,S)-diol 5 in >95% ee. Use of (DHQD)2-PHAL also afforded (R,R)-diol 5 as the major product in >95% ee, however, lower selectivity for the 6,7-position was observed in this case. The isomeric β-farnesene (9) resulted in a preference for the 10,11-olefin forming predominantly diol 11.

farnesene - asymmetric dihydroxylation - polyene