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.

Diastereo- and enantioselective synthesis of 1,2-diols by V(II)-promoted pinacol cross coupling

R. Annunziata
Primo
;
M. Benaglia
Secondo
;
M. Cinquini;F. Cozzi
Penultimo
;
1991

Abstract

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.
Settore CHIM/06 - Chimica Organica
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/187788
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