Cu(OTf)2-catalyzed ring-opening of epoxides with anilines: A convenient synthesis of β-amino alcohols

✍ Scribed by Hou Xue-Long; Wu Jie; Dai Li-Xin

• Publisher: John Wiley and Sons
• Year: 2010
• Tongue: English
• Weight: 260 KB
• Volume: 16
• Category: Article
• ISSN: 0256-7660
• DOI: 10.1002/cjoc.19980160612

✦ Synopsis

Cu( OTf)z=catalyzed ring-opening of epoxides with anilines: A convenient synthesis of p-amino alcohols HOU, Xue-Long*(#ZltR) W, Jie(!&M) DAI, Li-Xin(#P@) f . a ~t w v of +~omctdlic Chemi~trv, Shanghai InatitUteof Chyanu Chcmutry, C h i n u c Academy of Seimar, Shanghai 600082, Chino Aktrmzt by copper(I1) triflate prwida the corresponding /?-.mino dcohok in uwllent yieldr.

Keyword.

The nginukctiw ring-opening of epoxida with aniline and pchlororniliie catdyxed

Copper(I1) triflrk, ring-opening, epoxida, &amino alcohols @Amino alcohols are compounds of undoubted synthetic interest in organic chemistry. The most straightforward route to in amino alcohols involves the regioselective ring opening reaction of oxiranes' with excess amin-at elevated temperature. Although metal amides have been employed2 for such a transformation, a prior conversion of amines to metal amides certainly po%sessea some restriction in terms of the utility of this reaction on a large scale. The most effective and direct way is metal catalyzed opening of epoxides with aminea and by far only metal complexes CoC12: Yb(OTf)s,' and SmC1s5 were reported to be usable as catalyst. In the course of studying the synthesis and applications of epoxides? we found that copper(I1) triflate was also an