105563-10-8Relevant articles and documents
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.
