[CasualTech]

I was wondering if anyone had any insight into a method for regioselective epoxide opening with primary amines.  My target is a beta-amino alcohol with the epoxide being the commercially available 1,2-epoxy-3-phenoxypropane.  I am attempting to open up from the least hindered terminal end of the epoxide, however I am finding that primary amines show bad regioselectivity.  My last resort is Boc-protection and subsequent treating with NaH, however I have read that epoxides readily undergo rearrangement to allylic alcohols under these basic conditions.

[zarhym]

http://www.organic-chemistry.org/synthesis/C1N/amines/betaaminoalcohols.shtm

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