Enantioselective synthesis of the alcohol 'arm' for the ether compounds

[alintheopen]

Paucity of TMS-CN, lack of preparative chiral HPLC and a passion for enantioselective synthesis has led me to consider an alternative route to the alcohol side chain required for the chiral ether compounds (e.g. MMV670652).
Based on PhD work that I did with Aurélien Bigot and Matthew J Gaunt, I'm working on an catalytic enantioselective route to this side chain. Based on (http://pubs.acs.org/doi/abs/10.1021/ja206047h) and the route below:

[alintheopen]

Synthesis of Iodonium Salt:
Synthesis of (3,4-difluorophenyl)(mesityl)iodonium triflate (AEW 128-1)(http://malaria.ourexperiment.org/uri/54c)

Synthesis of N-acyl-oxazolidinone:
Synthesis of 3-(2-(Benzyloxy)acetyl)oxazolidin-2-one (AEW 129-1)(http://malaria.ourexperiment.org/uri/558)

[mattodd]

Lovely chemistry. Freon gas?

[alintheopen]

yeah...no Freon! Scheme is copied and pasted from the earlier CRO route. We may not introduce CHF2 anymore but focus on other more synthetically accessible ethers instead.

[david1597]

Info is installed on the wiki.

See also another possible route to enantioselective compounds.

Closing issue.