you need the diol? because if not, you can use Cp2TiCl. this maner you can have the deoxigenation products or the corresponding alcohols in presence of a good hydrogen-atom donor.

Andersen,

Please read this microreview

---Simona Bonollo, Daniela Lanari and Luigi Vaccaro, Ring-Opening of Epoxides in Water, 2011(14), 2587-2598 (2011)

hope that you will find an answer

You will find that The use of a polymeric CoIII-(salen) complex was reported by Zheng et al. in organic solvent or under solvent-free conditions. These Authors showed that better

ee-s were achieved for the preparation of diols when the recovered catalyst was used with water as reaction medium and as reactant.

---Y. Song, X. Yao, H. Chen, C. Bai, X. Hu, Z. Zheng, Tetrahedron Lett. 2002, 42, 6625–6627.

Good luck

Epoxide first convert to helo hydrine via HCl or HBr and HI then helo hydrine convert to Diol present of water and alkali.

Andersen,

Please note that polymer-​supported metal (Fe or Ru) complexes for epoxide ring opening reactions were successfully prepd. by anchoring the bis(2-​picolyl)​amine ligand onto the polymer poly(chloromethylstyrene-​co-​divinylbenzene) (PCD)​; the catalysts showed heterogeneous catalytic activity and easy recyclability in the ring opening reactions of various epoxide substrates with methanol or H2O at room temp. under mild and neutral conditions. See

---Lee, Sun Hwa et al., New Journal of Chemistry, 31, 1579-1582 (2007).

For biotransformation see

---Wistuba, D. et al., Chirality, 4, 185-92 (1992)

---Botes, Adriana Leonora et al., PCT Int. Appl., 2005100578, 27 Oct 2005

Good luck

Very easy, use hydroxide base.

@Burke

Andersen wrote

"Is it possible to open an epoxide to give the corresponding diol under basic/neutral conditions?

I need to open an epoxide on a complex molecule with a primary TBDMS group"

***Do not you think that hydroxide base will cleave the primary TBDMS group in such molecule?

Use a low concentrated hydroxide solution under mild conditions, and see does it open without touching the TBDMS group.

Opening an epoxide is usually done using an acid which converts it to halohydrin & the halogen is then substituted by a hydroxyl coming from a base. If a a base is used first , the ring will open to give anions at both ends & you need to try to acidify them both. Good luck.

Simple reagent methanolic hcl

Epoxide can be opened by aq. NaOH to get diol , the reaction of SN2 type.