Asymmetric synthesis of trans-3,4-dialkyl-gamma-butyrolactones via an acyl-Claisen and iodolactonization route.
[reaction: see text] A new, efficient, and general asymmetric synthesis of enantiomerically pure trans-3,4-dialkyl-gamma-lactones has been developed. The key steps are (1) copper-catalyzed three-component coupling of chiral amine, aldehyde, and alkyne, (2) acyl-Claisen rearrangement, and (3) iodolactonization. The products, chiral gamma-lactones, are versatile synthetic intermediates and structural units of natural products and modified nucleosides.
Department of Chemistry and Chemical Biology, Northeastern University, Boston, Massachusetts 02115, USA.
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D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D001688:Biological Products / Q000138:chemical synthesis / Q000737:chemistry; D002384:Catalysis; D003300:Copper / Q000737:chemistry; D003500:Cyclization; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry*; D009705:Nucleosides / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
D001688:Biological Products; D007783:Lactones; D009705:Nucleosides; D003300:Copper; D015107:4-Butyrolactone