| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 5226975 | Tetrahedron | 2007 | 8 Pages |
Abstract
Asymmetric Horner-Wadsworth-Emmons reactions of selected meso-α-dicarbonyl compounds with chiral phosphonate reagents, which possessed axially dissymmetric 1,1â²-bi-2- or 8-naphthol at the carboxylate moiety as a chiral auxiliary, were examined. The reactions proceeded smoothly with good chemical yields as well as with high diastereoselectivities. Z-olefins were preferentially formed, and it was found that the free hydroxy group at the 2â²- or 8â²-position on the naphthalene ring plays a crucial role in the high diastereoselectivity, probably due to a complex-induced proximity effect. Mechanistic considerations are also described.
Graphical abstract
Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Daiki Monguchi, Yoshihisa Ohta, Tatsuya Yoshiuchi, Toshiyuki Watanabe, Takumi Furuta, Kiyoshi Tanaka, Kaoru Fuji,