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 |
Autori: | ANNUNZIATA, RITA MARIA (Primo) BENAGLIA, MAURIZIO (Secondo) COZZI, FRANCO (Penultimo) |
Settore Scientifico Disciplinare: | Settore CHIM/06 - Chimica Organica |
Data di pubblicazione: | 1991 |
Rivista: | |
Tipologia: | Article (author) |
Digital Object Identifier (DOI): | http://dx.doi.org/10.1016/S0040-4020(01)86526-1 |
Appare nelle tipologie: | 01 - Articolo su periodico |