title: Synthesis of aromatic sphingosine analogues by diastereoselective amination of enantioenriched trans-γ,δ-unsaturated β-hydroxyesters.
abstract: An effective route to N-Boc-protected aromatic sphingosine analogues is accomplished. The strategy is based on the diastereoselective amination of enantioenriched trans-γ,δ-unsaturated β-hydroxyesters to establish anti,N-Boc-α-hydrazino-β-hydroxyesters. Nonreductive E1cB elimination is essential for the successful N-N bond cleavage of hydrazine while preserving the trans double bond. Either the (3R,2S) and (3S,2R) enantiomer of N-Boc-protected sphingosine analogues has been synthesized in five steps with excellent optical purity with ∼99% ee and >99% de.
authors.affiliation: Department of Chemistry and Biochemistry, Institute of Arctic Biology, University of Alaska , Fairbanks, Alaska 99775, United States.
authors.forename: Zhipeng
authors.initials: Z
authors.lastname: Dai
authors.forename: Thomas K
authors.initials: TK
authors.lastname: Green
mesh_terms: D000586:Amination; D004952:Esters; D006834:Hydrazines / Q000138:chemical synthesis* / Q000737:chemistry; D013110:Sphingosine / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D004952:Esters; D006834:Hydrazines; D013110:Sphingosine