Chemical Forums

Chemistry Forums for Students => Organic Chemistry Forum => Organic Chemistry Forum for Graduate Students and Professionals => Topic started by: CasualTech on December 16, 2015, 11:46:53 AM

Title: Regioselective epoxide opening with primary amines
Post by: CasualTech on December 16, 2015, 11:46:53 AM

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.

Title: Re: Regioselective epoxide opening with primary amines
Post by: zarhym on January 31, 2016, 11:30:13 PM

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

You will surly enjoy this.