The V(II) promoted pinacol cross coupling of a chiral aromatic aldehyde with chiral aliphatic aldehydes occurs to afford syn diols in up to 91:9 diastereoisomeric ratio and up to 84% enantiomeric excess. The pinacol coupling of (S)-lactaldehyde and (R)-glyceraldehyde derivatives has also been studied and matching and mis-matching pairs have been identified. The stereochemistry of the products was established by correlation. The sense and degree of stereoselection is discussed.
Diastereo- and enantioselective synthesis of 1,2-diols by V(II)-promoted pinacol cross coupling / R. Annunziata, M. Benaglia, M. Cinquini, F. Cozzi, P. Giaroni. - In: TETRAHEDRON. - ISSN 0040-4020. - 47:30(1991), pp. 5737-5758.
|Titolo:||Diastereo- and enantioselective synthesis of 1,2-diols by V(II)-promoted pinacol cross coupling|
ANNUNZIATA, RITA MARIA (Primo)
BENAGLIA, MAURIZIO (Secondo)
COZZI, FRANCO (Penultimo)
|Settore Scientifico Disciplinare:||Settore CHIM/06 - Chimica Organica|
|Data di pubblicazione:||1991|
|Digital Object Identifier (DOI):||http://dx.doi.org/10.1016/S0040-4020(01)86526-1|
|Appare nelle tipologie:||01 - Articolo su periodico|