Iterative Cr-mediated catalytic asymmetric allylation to synthesize syn/syn- and anti/anti-1,3,5-triols.

Iterative use of Cr-mediated catalytic asymmetric allylation could give a simple access to 1,3-polyols. Using syn/syn- and anti/anti-1,3,5-triols as representative examples, the feasibility of this approach is studied, thereby demonstrating that (1) the pre-existing TMS-protected alcohol at the beta-position does not give a significant effect on the Cr-mediated catalytic asymmetric allylation and (2) this synthetic route furnishes the expected syn/syn- and anti/anti-1,3,5-triols at the useful level of asymmetric induction and yield.