Highly selective allylborations of aldehydes using α,α-disubstituted allylic pinacol boronic esters.
Angew Chem Int Ed Engl
; 53(24): 6145-9, 2014 Jun 10.
Article
em En
| MEDLINE
| ID: mdl-24799283
ABSTRACT
α,α-Disubstituted allylic pinacol boronic esters undergo highly selective allylborations of aldehydes to give tetrasubstituted homoallylic alcohols with exceptional levels of anti-Z-selectivity (>201). The scope of the reaction includes both acyclic and cyclic allylic boronic esters which lead to acyclic and exocyclic tetrasubstituted homoallylic alcohols. The use of ß-borylated allylic boronic esters gave fully substituted alkenes bearing a boronic ester which underwent further cross-coupling enabling a highly modular and stereoselective approach to the synthesis of diaryl tetrasubstituted alkenes. Computational analysis revealed the origin of the remarkable selectivity observed.
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01-internacional
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MEDLINE
Assunto principal:
Boro
/
Aldeídos
/
Alcenos
/
Ésteres
Idioma:
En
Ano de publicação:
2014
Tipo de documento:
Article