879480-19-0Relevant academic research and scientific papers
Synthesis of α-diazo-β-hydroxyesters through a one-pot protocol by phase-transfer catalysis: Application to enantioselective aldol-type reaction and diastereoselective synthesis of α-amino-β-hydroxyester derivatives
Hasegawa, Kazuya,Arai, Shigeru,Nishida, Atsushi
, p. 1390 - 1401 (2007/10/03)
The one-pot synthesis of α-diazo-β-hydroxyesters from sodium azide under phase-transfer-catalyzed conditions has been achieved. This protocol includes three different chemical transformations promoted by a single catalyst in each step to give products in good to excellent yields. The reaction was applied to a catalytic asymmetric aldol-type reaction using α-diazoesters with aldehydes in the presence of a chiral quaternary ammonium salt and gave products with up to 81% ee. The diastereoselective transformation of the products to chiral α-amino-β-hydroxyester derivatives is also described.
