Asymmetric Synthesis of 2-Alkyl-4-hydroxycyclohex-2-en-1-ones by Scandium(III) Triflate Catalyzed Fragmentation of 2-Alkyl-3-iodo-1-oxocyclohexan-2,4-carbolactones.

Abstract Fragmentation of (2 S ,3 S ,4 S )-2-allyl-3-iodo-1-oxocyclohexan-2,4-carbolactone to (4 S )-2-allyl-4-hydroxycyclohex-2-en-1-one, a chiral building block of (−)-platensimycin, proceeded efficiently by using scandium(III) triflate in DMF–H 2 O (1:3) at 100 °C.