Abstract:
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.