| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 5274479 | Tetrahedron Letters | 2008 | 4 Pages |
Abstract
Hydroboration-oxidation of 1,1-disubstituted alkenes with borane-methyl sulfide complex in bridged tricyclic intermediates of the CP-225,917 ring system were observed to produce significant quantities of tertiary alcohol products. This net Markovnikov addition of water across an alkene is influenced by a combination of remote functional groups. Computations at the B3LYP/6-31Gâ level of theory correctly predicted this reversal in selectivity and directed the selective removal of functional groups to restore selectivity for the primary alcohol.
Graphical abstractRemote functional groups influence hydroboration of an exocyclic olefin leading to higher than expected levels of 3° alcohol products.Download full-size image
Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
James A. Ashenhurst, James L. Gleason,