Selective ring expansion alkylation of formyl[2.2.1]bicyclic carbinols with C-nucleophiles: a unique route to cyclopentane derivatives.
Reactions of camphor-, and camphene-derived formyl [2.2.1]bicyclic carbinols with Grignard and organolithium reagents afford the corresponding regio- and stereospecific alkyl/aryl [3.2.1]bicyclic diols. Some of these bicyclic diols have been treated with lead tetraacetate to provide new chiral cyclopentane derivatives. A plausible mechanism of the ring expansion-alkylation reaction is proposed.
Department of Applied Chemistry, Chaoyang University of Technology, Wufong, 413, Taichung, Taiwan, ROC. tfyang@cyut.edu.tw
Te-Fang
TF
Yang
Chih-Hao
CH
Tseng
Kuan-I
KI
Wu
Chung-Nien
CN
Chang