Enantioselective C-C bond cleavage creating chiral quaternary carbon centers.
[Structure: see text] A chiral all-carbon benzylic quaternary carbon center is created by the asymmetric intramolecular addition/ring-opening reaction of a boryl-substituted cyclobutanone, which involves enantioselective beta-carbon elimination from a symmetrical rhodium cyclobutanolate. The asymmetric reaction was successfully applied to a synthesis of sesquiterpene, (-)-alpha-herbertenol.
Matsuda
Takanori
T
Department of Synthetic Chemistry & Biological Chemistry, Kyoto University, Katsura, Kyoto 615-8510, Japan.
Shigeno
Masanori
M
Makino
Masaomi
M
Murakami
Masahiro
M
D002244:Carbon / Q000737:chemistry; D002384:Catalysis; D003517:Cyclopentanes / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010636:Phenols / Q000138:chemical synthesis* / Q000737:chemistry; D012238:Rhodium / Q000737:chemistry; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D003517:Cyclopentanes; D010636:Phenols; D012717:Sesquiterpenes; C482284:herbertenol; D002244:Carbon; D012238:Rhodium