One-pot catalytic asymmetric synthesis of pyranones.
Enantioenriched pyranones are important intermediates in the synthesis of natural products and the generation of compound libraries. A one-pot method for their synthesis is outlined. Catalytic asymmetric alkylation of 2-furfurals in the presence of catalytic (-)-MIB generates enantioenriched furyl zinc alkoxides. Addition of water/THF followed by NBS results in formation of pyranones with ee's >90% and yields between 46-77%.
Cheng
Kevin
K
P. Roy and Diana T. Vagelos Laboratories, University of Pennsylvania, Department of Chemistry, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323, USA.
Kelly
Ann Rowley
AR
Kohn
Rachel A
RA
Dweck
Jessica F
JF
Walsh
Patrick J
PJ
D000478:Alkylation; D002384:Catalysis; D005662:Furaldehyde / Q000737:chemistry; D005663:Furans / Q000737:chemistry; D015394:Molecular Structure; D011753:Pyrones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D015032:Zinc / Q000737:chemistry
D005663:Furans; D011753:Pyrones; D005662:Furaldehyde; D015032:Zinc