2-Vinyl Threoninol Derivatives via Acid-Catalyzed Allylic Substitution of Bisimidates.
A diastereoselective synthesis of 4-vinyl oxazolines syn-2 was developed based on an acid-catalyzed cyclization of bistrichloroacetimidates (E)-1. The reaction likely involves an allyl carbenium ion intermediate in which the adjacent stereocenter directs the stereoselectivity for C-N bond formation. Oxazolines syn-2 were transformed to C-quaternary threoninol, threoninal, and threonine derivatives which can be further incorporated into complex natural compounds.
Latvian Institute of Organic Synthesis, Aizkraukles 21, Riga, Latvia LV 1006.
Varun
V
Kumar
Latvian Institute of Organic Synthesis, Aizkraukles 21, Riga, Latvia LV 1006.
Kristine
K
Klimovica
Latvian Institute of Organic Synthesis, Aizkraukles 21, Riga, Latvia LV 1006.
Dace
D
Rasina
Latvian Institute of Organic Synthesis, Aizkraukles 21, Riga, Latvia LV 1006.
Aigars
A
Jirgensons
D000498:Allyl Compounds / Q000737:chemistry*; D000605:Amino Alcohols / Q000737:chemistry*; D002072:Butylene Glycols / Q000737:chemistry*; D003500:Cyclization; D007096:Imidoesters / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010080:Oxazoles / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000737:chemistry*
C000605072:2-vinyl threoninol; D000498:Allyl Compounds; D000605:Amino Alcohols; D002072:Butylene Glycols; D007096:Imidoesters; D010080:Oxazoles; D014753:Vinyl Compounds; C532652:threoninol