500352-90-9Relevant articles and documents
Synthesis of chiral ligands derived from the Betti base and their use in the enantioselective addition of diethylzinc to aromatic aldehydes
Lu, Jun,Xu, Xuenong,Wang, Cunde,He, Jiangang,Hu, Yuefei,Hu, Hongwen
, p. 8367 - 8369 (2002)
A novel procedure for selective direct N,N-alkylation of the chiral Betti base was developed, and a new family of chiral ligands, (S)-1-(α-cycloaminobenzyl)-2-naphthols, were prepared. The ligands with five- and six-membered cyclic amines showed highly efficient asymmetric induction in the addition of diethylzinc to aromatic aldehydes in 93-96% yields and 91-99% ee.
Novel preparation of non-racemic 1-[α-(1-azacycloalkyl)benzyl]-2naphthols from Betti base and their application as ehiral ligands in the asymmetric addition of diethylzinc to aryl aldehydes
Lu, Jun,Xu, Xuenong,Wang, Shaozhong,Wang, Cunde,Hu, Yuefei,Hu, Hongwen
, p. 2900 - 2903 (2007/10/03)
A novel route for the preparation of non-racemic 1-[α-(1-azacycloalkyl)benzyl]-2-naphthols was developed, which involves regioselective N-cycloalkylation of the Betti base with dials in the presence of NaBH3CN to give 1-azacycloalka[2,1-b]oxazine followed by the selective cleavage of a C-O bond with LiAlH4. As a new family of chiral ligands, their application in the enantioselective addition of diethylzinc to aryl aldehydes was tested. The ligands incorporating pyrrolidine and piperidine led to highly efficient asymmetric induction to give products in up to 96% yield and 99% ee.
