158380-79-1Relevant academic research and scientific papers
Stereoselective Synthesis of (2S,3S)-Norstatine Derivatives by Addition of Lithiated Methoxyallene to Amino Aldehydes and Subsequent Ozonolysis
Hormuth, Stephan,Reissig, Hans-Ulrich,Dorsch, Dieter
, p. 121 - 128 (2007/10/02)
Addition of lithiated methoxyallene 2 to optically active N-benzyl-Boc-protected amino aldehydes 12-14 and to aldehyde 16 provides products 17-20 with good to excellent diastereoselectivity.These adducts are subsequently cleaved by ozonolysis to give α-hydroxy-β-amino acid derivatives 21-25 in good overall yield.By conversion into an oxazolidone derivative, the configuration of the major diastereomer was determined to be anti (2S,3S).Thus, the additions of 2 follow the course proposed by the Felkin-Anh model and are not ruled by chelation effects.The diastereoselective synthesis of 22 constitutes one of the simplest routes to a protected norstatine derivative. - Key Words: Methoxyallene / Allenes / Aldehydes, α-amino / Lithium compounds / Ozonolysis / Norstatine derivatives
