| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1348086 | Tetrahedron: Asymmetry | 2008 | 8 Pages |
A Pd-catalyzed asymmetric allylic alkylation of 2-substituted cycloalkenyl carbonates using a chiral diaminophosphine oxide is described. Asymmetric allylic substitution of various cyclic substrates proceeded using 5 mol % of Pd catalyst, 10 mol % of (S,RP)-Ph-DIAPHOX 1, 10 mol % of LiOAc, and N,O-bis(trimethylsilyl)acetamide (BSA), to afford the corresponding products in excellent yields with up to 92% ee.
Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slide
(1R)-2-Phenyl-2-cyclohexen-1-yl malonic acid dibenzyl esterC29H28O4Ee = 86%[α]D24=-35.4 (c 0.32, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (R)
(1R)-2-Phenyl-2-cyclopenten-1-yl malonic acid dibenzyl esterC28H26O4Ee = 89%[α]D19=-43.2 (c 0.87, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (R)
