Enantioselective bromolactonization using an S-alkyl thiocarbamate catalyst.
The apple never falls far from the tree: S-alkyl thiocarbamate 1 (see scheme, NBP = N-bromophthalimide) was prepared in high yield through a synthetic sequence involving a Newman-Kwart rearrangement of the corresponding O-alkyl thiocarbamates. Compound 1 was used to catalyze bromolactonization, thus providing enantioenriched δ-lactones in excellent yield and enantioselectivity.
Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543, Singapore.
Xiaojian
X
Jiang
Chong Kiat
CK
Tan
Ling
L
Zhou
Ying-Yeung
YY
Yeung
D002384:Catalysis; D018360:Crystallography, X-Ray; D006842:Hydrocarbons, Brominated / Q000138:chemical synthesis* / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism; D013859:Thiocarbamates / Q000138:chemical synthesis / Q000737:chemistry*
D006842:Hydrocarbons, Brominated; D007783:Lactones; D013859:Thiocarbamates