A highly stereoselective reductive amination of 3-ketosteroid with amines: an improved synthesis of 3α-aminosteroid

• Published in: Tetrahedron letters Vol. 46; no. 45; pp. 7675 - 7678
• Main Authors: Nawaz Khan, Sharaf, Bae, Seon-Yun, Kim, Hong-Seok
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 07.11.2005; Elsevier
• Subjects: 3α-Aminosteroid; Chemistry; Chemistry, Organic; Physical Sciences; Reductive amination; Science & Technology; Stereoselective; Reductive amination; 3α-Aminosteroid; Stereoselective; SODIUM-BOROHYDRIDE; KETONES; reductive amination; REDUCING AGENT; 3 alpha-aminosteroid; TITANIUM(IV) ISOPROPOXIDE; IMINES; ALDEHYDES; SQUALAMINE; stereoselective; EFFICIENT
• ISSN: 0040-4039; 1873-3581
• DOI: 10.1016/j.tetlet.2005.09.051

A highly stereoselective reductive amination method was developed based on in situ generated sodium acyloxyborohydride and was successfully applied to a steroidal skeleton with various amine sources. High yield (96%) and a de of up to 95% were achieved by modifying the reducing reagent. The effect of this reagent will be discussed. A highly stereoselective reductive amination method was developed based on in situ generated sodium acyloxyborohydride and was successfully applied to a steroidal skeleton with various amine sources. High yield (96%) and a de of up to 95% were achieved by modifying the reducing reagent. The effect of this reagent will be discussed.