Chirality transfer from guanidinium ylides to 3-alkenyl (or 3-alkynyl) aziridine-2-carboxylates and application to the syntheses of (2R,3S)-3-hydroxyleucinate and D-erythro-sphingosine.
[Reaction: see text]. Reaction of chiral guanidinium ylides with alpha,beta-unsaturated aldehydes gives 3-(alpha,beta-unsaturated) aziridine-2-carboxylates in high diastereo- and enantioselectivities (up to 93% diastereomeric excess and 98% enantiomeric excess). 3-(1-methylvinyl)- and 3-[(E)-pentadec-1-enyl]aziridine-2-carboxylates were successfully employed to prepare (2R,3S)-3-hydroxyleucinate and d-erythro-sphingosine, respectively.
Disadee
Wannaporn
W
Graduate School of Pharmaceutical Sciences, Chiba University, Inage, Chiba 263-8522, Japan.
Ishikawa
Tsutomu
T
D000447:Aldehydes / Q000737:chemistry; D001388:Aziridines; D019791:Guanidine / Q000737:chemistry*; D007930:Leucine / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D013110:Sphingosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis
D000447:Aldehydes; D001388:Aziridines; C481931:erythro-(2R,3S)-sphingosine; C073440:aziridine-2-carboxylic acid; D007930:Leucine; D019791:Guanidine; D013110:Sphingosine