1107650-29-2Relevant academic research and scientific papers
Umpolung Synthesis of 1,3-Amino Alcohols: Stereoselective Addition of 2-Azaallyl Anions to Epoxides
Daniel, Paige E.,Weber, Alexandria E.,Malcolmson, Steven J.
, p. 3490 - 3493 (2017)
We report the direct preparation of 1,3-amino alcohols that contain up to three contiguous stereogenic centers by the umpolung coupling of imines and epoxides. Nucleophilic 2-azaallyl anions, generated from imines, are stereoselectively added to epoxides to furnish 1,3-amino alcohols after hydrolysis of the product imine. Transformations afford amino alcohols with >98% site selectivity with respect to both reaction partners and in up to >98% yield and >20:1 dr.
Exploring substrate scope of Shi-type epoxidations
Nieto, Natalia,Munslow, Ian J.,Fernández-Pérez, Héctor,Vidal-Ferran, Anton
experimental part, p. 2856 - 2858 (2009/05/07)
Enantioselective epoxidations of alkenes (12 examples) were achieved using a Shi-type carbohydrate-derived hydrate and Oxone. The chiral platform provided by the catalyst tolerates a wide range of substituents providing high yields and enantioselectivities (80-95.5% ee). However, styrene derivatives were only converted with poor selectivities (11-26% ee). Georg Thieme Verlag Stuttgart.
