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Is a hydrogen bonded carbene an intermediate in the organoaluminum-induced ring opening of pyranosides?
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- Olsson, Roger (author)
- Lund University,Lunds universitet,Kemiska institutionen,Institutioner vid LTH,Lunds Tekniska Högskola,Department of Chemistry,Departments at LTH,Faculty of Engineering, LTH
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- Berg, Ulf (author)
- Lund University,Lunds universitet,Kemiska institutionen,Institutioner vid LTH,Lunds Tekniska Högskola,Department of Chemistry,Departments at LTH,Faculty of Engineering, LTH
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- Frejd, Torbjörn (author)
- Lund University,Lunds universitet,Kemiska institutionen,Institutioner vid LTH,Lunds Tekniska Högskola,Department of Chemistry,Departments at LTH,Faculty of Engineering, LTH
- (creator_code:org_t)
- 1997
- 1997
- English 4 s.
- In: Tetrahedron Letters. - 0040-4039. ; 38:32, s. 5701-5704
- Journal article (peer-reviewed)
Abstract
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- Semiempirical and ab initio quantum chemical computations indicate that the intermediate formed prior to the selectivity-determining methyl transfer step in the reaction between glycosides and trimethylaluminum is a strongly hydrogen-bended equilibrium OH...C = O-H...C, which is proposed to be an important selectivity promoting factor in the alkyl transfer reaction.
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