Stereodivergent total asymmetric synthesis of polyhydroxylated pyrrolidines via tandem allylic epoxidation and intramolecular cyclization reactions |
| |
| Authors: | Satwinder Singh |
| |
| Institution: | Department of Chemistry, The University of Texas at San Antonio, 6900 N. Loop 1604 West, San Antonio, TX 78249, USA |
| |
| Abstract: | Epoxidation of the allylic alcohols 10 and 11 using the VO(acac)2/t-BuOOH system followed by an intramolecular 5-exo cyclization of the resulting δ-epoxycarbamates 12, 13, 18, and 19 has been shown to provide a general and efficient solution for the asymmetric synthesis of polyhydroxy pyrrolidines. The requisite vicinal amino alcohol functionality was enantio-/regio-selectively installed by the Os-catalyzed asymmetric aminohydroxylation reaction of the designed achiral olefin 6. |
| |
| Keywords: | Polyhydroxylated pyrrolidines Regioselective asymmetric aminohydroxylation Allylic epoxidation Intramolecular cyclization |
| 本文献已被 ScienceDirect 等数据库收录！ |
|
