Dynamic Kinetic Resolution of Homoallylic Alcohols : Application to the Synthesis of Enantiomerically Pure 5,6-Dihydropyran-2-ones and delta-Lactones

• Dynamic kinetic resolution of various homoallylic alcohols with the use of Candida antarctica lipaseB and ruthenium catalyst 2 afforded homoallylic acetates in high yields and with high enantioselectivity. These enantiopure acetates were further transformed into homoallylic acrylates after hydrolysis of the ester function and subsequent DMAP-catalyzed esterification with acryloyl chloride. After ring-closing metathesis 5,6-dihydropyran-2-ones were obtained in good yields. Selective hydrogenation of the carboncarbon double bond afforded the corresponding -lactones without loss of chiral information.

Ämnesord

NATURVETENSKAP  -- Kemi -- Organisk kemi (hsv//swe)

NATURAL SCIENCES  -- Chemical Sciences -- Organic Chemistry (hsv//eng)

Nyckelord

dynamic kinetic resolution

homoallylic alcohols

lactones

racemization

ruthenium catalysis

Publikations- och innehållstyp

ref (ämneskategori)

art (ämneskategori)