EFFICIENT INTRAMOLECULAR C-H INSERTION BY AN ALKYLIDENE CARBENE GENERATED FROM A VINYL-CHLORIDE

Authors
TABER DF SAHLI A YU H MEAGLEY RP
Citation
Df. Taber et al., EFFICIENT INTRAMOLECULAR C-H INSERTION BY AN ALKYLIDENE CARBENE GENERATED FROM A VINYL-CHLORIDE, Journal of organic chemistry, 60(20), 1995, pp. 6571-6573
Citations number
53
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
60
Issue
20
Year of publication
1995
Pages
6571 - 6573
Database
ISI
SICI code
0022-3263(1995)60:20<6571:EICIBA>2.0.ZU;2-R
Abstract
It is observed that chloride 4 on exposure to sodium bis(trimethylsily l)amide smoothly generates the cyclopentene 5, by insertion of the int ermediate alkylidene carbene into the methine C-H. Chloride 4 is prepa red in several steps from L-tartaric acid. On ozonolysis and subsequen t aldol condensation, 5 is transformed into 1, a synthon for the A rin g of taxol 2.