139964-98-0Relevant academic research and scientific papers
Aziridine-modified amino alcohols as efficient modular catalysts for highly enantioselective alkenylzinc additions to aldehydes
Braga, Antonio L.,Paixao, Marcio W.,Westermann, Bernhard,Schneider, Paulo H.,Wessjohann, Ludger A.
, p. 917 - 920 (2007)
N-Tritylaziridino alcohols have been easily synthesized in a straightforward synthetic route from an inexpensive and easily available chiral pool. They were used in the enantioselective alkenylzinc additions to aldehydes furnishing the products in excelle
A positional scanning approach to the discovery of dipeptide-based catalysts for the enantioselective addition of vinylzinc reagents to aldehydes
Sprout, Christopher M.,Richmond, Meaghan L.,Seto, Christopher T.
, p. 7408 - 7417 (2007/10/03)
A combinatorial library of dipeptide N-acylethylenediamine-based ligands was synthesized by parallel solid-phase methods. These ligands were screened in crude form as catalysts for the asymmetric addition of vinylzinc reagents to aldehydes to give chiral allylic alcohols. Three sites of diversity on the ligands were optimized using a positional scanning approach. The optimized structure from the library, ligand 54, was found to catalyze the formation of 10 different (E)-allylic alcohols with enantioselectivities ranging from 90% to 95% ee. This ligand was effective for both aromatic and α-branched aldehydes, and vinylzinc reagents derived from both bulky and straight chain terminal alkynes.
Enantioselective addition of vinylzinc reagents to aldehydes catalyzed by modular ligands derived from amino acids
Richmond, Meaghan L.,Sprout, Christopher M.,Seto, Christopher T.
, p. 8835 - 8840 (2007/10/03)
A series of N-acylethylenediamine-based ligands were synthesized from Boc-protected amino acids. The ligands were screened for the ability to catalyze the asymmetric addition of vinylzinc reagents to aldehydes. Three sites of diversity on the ligands were optimized for this reaction using a positional scanning approach. The optimized ligand 3d was found to catalyze the formation of 15 different (E)-allylic alcohols with enantioselectivities that ranged from 52 to 91% ee and yields that ranged from 40 to 90%. This ligand was especially effective for the reaction of aromatic aldehydes with vinylzinc reagents derived from bulky terminal alkynes. Ligand 3d catalyzed the addition of (E)-(3,3-dimethylbut-1-enyl)(ethyl)zinc to 2-naphthaldehyde to give (R,E)-4,4-dimethyl-1-(naphthalene-1-yl)pent-2-en-1-ol in 89% ee. The ee of this product could be increased to 97% through a single recrystallization.
A general, highly enantioselective method for the synthesis of D and L α-amino acids and allylic amines
Chen, Young K.,Lurain, Alice E.,Walsh, Patrick J.
, p. 12225 - 12231 (2007/10/03)
Catalytic and enantioselective synthesis of amino acids is a subject of intense interest in the field of asymmetric catalysis. Traditionally, researchers have concentrated their efforts largely on the design and discovery of enantiopure catalysts for the
Catalytic Asymmetric Synthesis of Secondary (E)-Allyl Alcohols from Acetylenes and Aldehydes via (1-Alkenyl)zinc Intermediates
Oppolzer, Wolfgang,Radinov, Rumen N.
, p. 170 - 173 (2007/10/02)
Hydroboration of aliphatic 1-alkynes with freshly prepared dicyclohexylborane (1 mol-equiv., hexane), treatment of the resulting boranes 5 with Et2Zn or Me2Zn (1.05 mol-equiv.) followed by addition of (-)-3-exo-(dimethylamino)isoborneol (DA
