240429-81-6Relevant articles and documents
A new cysteine-derived ligand as catalyst for the addition of diethylzinc to aldehydes: The importance of a 'free' sulfide site for enantioselectivity
Braga, Antonio L.,Alves, Elenilson F.,Silveira, Claudio C.,Zeni, Gilson,Appelt, Helmoz R.,Wessjohann, Ludger A.
, p. 588 - 594 (2007/10/03)
New chiral sulfides and disulfides were synthesized from readily available and inexpensive cysteine by straightforward methods in order to elucidate the relative importance of the various donor atoms (N, O, S) available in free or alkylated form resulting in covalent or dative bonds to the metal, respectively. Their application in the addition of diethylzinc to aldehydes provides secondary alcohols with up to 99% ee, and S-configuration, when catalytic amounts of disulfide ligands with the ability to form an S-Zn bond were used. In contrast to this, benzyl alcohols with the opposite absolute configuration R could be achieved, albeit with decreased yield and enantioselectivity, by the use of alkylated sulfide ligands.
New C2-symmetric chiral disulfide ligands derived from (R)-cysteine
Braga, Antonio L,Appelt, Helmoz R,Schneider, Paulo H,Rodrigues, Oscar E.D,Silveira, Claudio C,Wessjohann, Ludger A
, p. 3291 - 3295 (2007/10/03)
Several sulfur-containing optically active C2-symmetrical ligands have been synthesized from (R)-cysteine and applied successfully as chiral catalysts in the asymmetric addition of diethylzinc to aldehydes. The resulting secondary alcohols could be obtained in good yields and excellent enantiomeric excess.
