Regioselective ring-opening of epoxides with ortho-lithioanisoles catalyzed by BF3 center dot OEt2
TETRAHEDRON, cilt.68, sa.32, ss.6463-6471, 2012 (SCI-Expanded, Scopus)
- Yayın Türü: Makale / Tam Makale
- Cilt numarası: 68 Sayı: 32
- Basım Tarihi: 2012
- Doi Numarası: 10.1016/j.tet.2012.05.116
- Dergi Adı: TETRAHEDRON
- Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
- Sayfa Sayıları: ss.6463-6471
- Süleyman Demirel Üniversitesi Adresli: Evet
Özet
It is presented that a number of o-2-hydroxyalkylanisoles could be efficiently synthesized through the regioselective ring-opening reaction of epoxides with o-lithioanisoles in the presence of BF3 center dot OEt2 Lewis-acid catalyst. Sterically demanding o-lithioanisoles had to be generated by exploiting the combination of (BuLi)-Bu-n and a catalytic amount of TMEDA (0.20 equiv) in Et2O as the lithiator whereas 'normal' anisole could be lithiated at ortho-position by treatment with (BuLi)-Bu-n in THE as usual. Surprisingly, the availability of THE and a catalytic amount of TMEDA (0.20 equiv) in the reaction mixture was found to enhance the reaction yields dramatically. A complex aggregate formation by the co-operative ligation of THF and TMEDA to ortho-lithioanisole(s) was proposed to rationalize the high reactivity achieved in the ring-opening reaction of epoxides. (C) 2012 Elsevier Ltd. All rights reserved.