110529-28-7Relevant articles and documents
Catalytic asymmetric alkylation of aldehydes by diethylzinc in the presence of N-iso-propylephedrine; dependence of enantioselectzvity on Et2Zn:RCHO
Chaloner, Penny A.,Langadianou, Eugenia
, p. 5185 - 5188 (1990)
The enantioselective alkylation of a range of aldehydes by diethylzinc in the presence of N-isopropylephedrine has been investigated. Both the yield and the enantioselectivity of the reaction was found to depend on the ratio of Et2Zn to the ald
Planar-chiral salen and hemisalen [2.2]paracyclophane ligands for asymmetric diethylzinc addition to aldehydes
Danilova, Tatyana I.,Rozenberg, Valeria I.,Starikova, Zoya A.,Braese, Stefan
, p. 223 - 229 (2004)
Fourteen multistereogenic symmetric and asymmetric salens based on a [2.2]paracyclophane skeleton have been tested as catalysts for the enantioselective addition of diethylzinc to aldehydes affording the corresponding alcohols in up to 94% enantiomeric excess. Chiral [2.2]paracyclophane hemisalens are applied for the first time as chiral ligands in the Et2Zn addition to benzaldehyde.
Novel chiral tridentate Schiff base ligands of the [2.2]paracyclophane series: Synthesis and application
Danilova, Tatyana I.,Rozenberg, Valeria I.,Sergeeva, Elena V.,Starikova, Zoya A.,Braese, Stefan
, p. 2013 - 2019 (2003)
The first example of the efficient application of chiral tridentate N,O-[2.2]paracyclophane ligands of the imino type for enantioselective diethylzinc addition to aliphatic and aromatic aldehydes is presented. The enantiomeric excess of the resulted secondary alcohols is up to 93% e.e.
N-trityl-aziridinyl(diphenyl)methanol as an effective catalyst in the enantioselective addition of diethylzinc to aldehydes
Lawrence, Corrine F.,Nayak, Sandip K.,Thijs, Lambertus,Zwanenburg, Binne
, p. 1571 - 1572 (1999)
High levels of enantioselectivity have been achieved in the diethylzinc addition to both aromatic and aliphatic aldehydes, employing N-trityl- aziridinyl(diphenyl)methanol as the chiral catalyst. The R- and S-antipodes of the catalyst can readily be prepa
Polymer-supported N-tritylaziridinyl(diphenyl)methanol as an effective catalyst in the enantioselective addition of diethylzinc to aldehydes
Ten Holte, Peter,Wijgergangs, Jan-Piet,Thijs, Lambertus,Zwanenburg, Binne
, p. 1095 - 1097 (1999)
(matrix presented) Novel polymer-supported N-tritylaziridino alcohol 2 was utilized as chiral ligand in the asymmetric addition of diethylzinc to aldehydes. High enantioselectivities were obtained for both aromatic and aliphatic aldehydes. The catalyst wa
Dynamic Kinetic Resolution of Alcohols by Enantioselective Silylation Enabled by Two Orthogonal Transition-Metal Catalysts
Oestreich, Martin,Seliger, Jan
, p. 247 - 251 (2020/10/29)
A nonenzymatic dynamic kinetic resolution of acyclic and cyclic benzylic alcohols is reported. The approach merges rapid transition-metal-catalyzed alcohol racemization and enantioselective Cu-H-catalyzed dehydrogenative Si-O coupling of alcohols and hydrosilanes. The catalytic processes are orthogonal, and the racemization catalyst does not promote any background reactions such as the racemization of the silyl ether and its unselective formation. Often-used ruthenium half-sandwich complexes are not suitable but a bifunctional ruthenium pincer complex perfectly fulfills this purpose. By this, enantioselective silylation of racemic alcohol mixtures is achieved in high yields and with good levels of enantioselection.
Kinetic resolution of racemic allylic alcoholsviairidium-catalyzed asymmetric hydrogenation: scope, synthetic applications and insight into the origin of selectivity
Wu, Haibo,Margarita, Cristiana,Jongcharoenkamol, Jira,Nolan, Mark D.,Singh, Thishana,Andersson, Pher G.
, p. 1937 - 1943 (2021/02/22)
Asymmetric hydrogenation is one of the most commonly used tools in organic synthesis, whereas, kinetic resolutionviaasymmetric hydrogenation is less developed. Herein, we describe the first iridium catalyzed kinetic resolution of a wide range of trisubstituted secondary and tertiary allylic alcohols. Large selectivity factors were observed in most cases (sup to 211), providing the unreacted starting materials in good yield with high levels of enantiopurity (ee up to >99%). The utility of this method is highlighted in the enantioselective formal synthesis of some bioactive natural products including pumiliotoxin A, inthomycin A and B. DFT studies and a selectivity model concerning the origin of selectivity are presented.
Enantioselective addition of diethylzinc to aldehydes catalyzed by 5-cis-substituted proline derivatives
Prause, Felix,Wagner, Stefan,Breuning, Matthias
, p. 94 - 101 (2018/11/30)
5-Cis-substituted prolinols, prolinamines, and prolinamine sulfonamides proved to be efficient ligands for the enantioselective addition of diethylzinc to aldehydes, providing up to 99% ee. The sense of asymmetric induction can be controlled by the nature
