158380-72-4Relevant academic research and scientific papers
Substrate-Controlled Diastereoselectivity Reversal in NHC-Catalyzed Cross-Benzoin Reactions Using N-Boc-N-Bn-Protected α-Amino Aldehydes
Haghshenas, Pouyan,Quail, J. Wilson,Gravel, Michel
, p. 12075 - 12083 (2016)
The effectiveness of utilizing N-Bn-N-Boc-α-amino aldehydes in cross-benzoin reactions with heteroaromatic aldehydes is demonstrated. The reaction is both chemoselective and syn-selective, making it complementary to the anti-selective cross-benzoin reaction of NHBoc-α-amino aldehydes. Good diastereoselectivity is obtained for a variety of amino aldehydes, including nonhindered ones. A Felkin-Anh model can be used to rationalize the observed diastereoselectivity.
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
