3542-12-9Relevant articles and documents
α-Amino Aldehydes as Readily Available Chiral Aldehydes for Rh-Catalyzed Alkyne Hydroacylation
Hooper, Joel F.,Seo, Sangwon,Truscott, Fiona R.,Neuhaus, James D.,Willis, Michael C.
, p. 1630 - 1634 (2016/02/20)
Readily available α-amino aldehydes, incorporating a methylthiomethyl (MTM) protecting group on nitrogen, are shown to be efficient substrates in Rh-catalyzed alkyne hydroacylation reactions. The reactions are performed under mild conditions, employing a small-bite-angle bis-phosphine ligand, allowing for good functional group tolerance with high stereospecificity. Amino aldehydes derived from glycine, alanine, valine, leucine, phenylalanine, isoleucine, serine, tryptophan, methionine, and cysteine were successfully employed, as was an enantiomerically enriched α-OMTM-aldehyde derived from phenyllactic acid. The synthetic utility of the α-amino enone products is demonstrated in a short enantioselective synthesis of the natural product sphingosine.
α-Amino Acid Derivatives as Chiral Educts for Asymmetric Products. Synthesis of Shpingosine from α'-Amino-α,β-ynones
Boutin, Raymond H.,Rapoport, Henry
, p. 5320 - 5327 (2007/10/02)
The utility of α'-amino-α,β-ynones in the chirospecific synthesis of sphingosine is demonstrated.Thus, a protected L-serine isoxazolidide has been converted to sphingosine by two routes, both via α,β-ynones.The first route is very short and high yielding, merely involving two selective reductions after synthesis the appropriate α,β-ynone.The second route involves alkylation of a β-unsubstituted ynone and illustrates the synthetic versatility of the α'-amino-α,β-ynone system.Further routes through conjugate 1,4-additions to ynones are demonstrated but are limited by the highly reactive nature of this system.
