160978-12-1Relevant articles and documents
Asymmetric synthesis of β-amino acids through application of chiral sulfoxide
Sivakumar,Babu,Bhat, Sujata V.
, p. 1095 - 1099 (2001)
This paper describes asymmetric synthesis of β-aminophenylpropionic acid through application of a homochiral sulfoxide auxiliary. High kinetically controlled (3R,2S,RS)-diastereoselectivity (-60°C) is achieved during addition of the lithium enolate of tert-butyl (+)-(R)-p-toluenesulfinylacetate to substituted N-(benzylidene)toluene-4-sulfonamides 2a-2d. The reductive cleavage of adduct 3a with sodium amalgam yielded tert-butyl 3-(toluene-4-sulfonamido)-3-phenylpropionate 5a, which was subjected to ester hydrolysis and subsequent detosylation with sodium in liquid ammonia to yield (S)-β-aminophenylpropionic acid in good yield and high 91% e.e.
Diastereoselective Addition of α-Sulfinyl Ester Enolate with Benzaldimines Possessing An Electron Withdrawing Group at the Nitrogen Atom
Shimizu, Makoto,Kooriyama, Yuuji,Fujisawa, Tamotsu
, p. 2419 - 2422 (1994)
The reaction of optically pure α-sulfinyl ester enolate with benzaldimines possessing an ewlectron withdrawing group at the nitrogen atom gave β-amino ester in both enantiomeric forms in satisfactory optical and chemical yields (up to 94percentee), in which the changeover of the diastereofacial selectivity was induced by suitable choice of the protecting group at the nitrogen and the use of additives.
A novel synthesis of the macrocyclic spermidine alkaloid (+)-(S)-dihydroperiphylline
Sergeyev, Sergey A.,Hesse, Manfred
, p. 161 - 167 (2007/10/03)
A novel, short, and highly stereoselective synthesis of the macrocyclic spermidine alkaloid (+)-(S)-dihydroperiphylline (15) is described. The key synthetic steps were the stereoselective addition of the chiral amine 1 to the cinnamate 2 and cyclization o
