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Enantioselective Synthesis of Cyanohydrin O ‐Phosphates Mediated by the Bifunctional Catalyst Binolam–AlCl
Author(s) -
Baeza Alejandro,
Casas Jesús,
Nájera Carmen,
Sansano José M.,
Saá José M.
Publication year - 2003
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200351552
Subject(s) - bifunctional , cyanohydrin , enantioselective synthesis , allylic rearrangement , catalysis , chemistry , enantiomer , enantiomeric excess , bifunctional catalyst , palladium , organic chemistry , combinatorial chemistry
( R )‐ and ( S )‐binolam–AlCl complexes act as bifunctional catalysts to mediate the enantioselective cyanophosphorylation of aldehydes at room temperature. The resulting chiral cyanohydrin O‐ phosphates can be reduced to β‐aminoalcohols or, when suitably substituted, can be transformed into γ‐cyanoallylic alcohols through palladium‐catalyzed allylic substitution, without loss of enantiomeric excess (see scheme).