Diastereoselectivity of additions to chiral carbonyl oxides
Dussault, PH; Zope, UR
| HERO ID | 1193209 |
|---|---|
| In Press | No |
| Year | 1995 |
| Title | Diastereoselectivity of additions to chiral carbonyl oxides |
| Authors | Dussault, PH; Zope, UR |
| Journal | Journal of Organic Chemistry |
| Volume | 60 |
| Issue | 25 |
| Page Numbers | 8218-8222 |
| Abstract | The influence of a resident stereocenter on the formation of hydroperoxy acetals from carbonyl oxides is investigated. Addition of either methanol or 2-propanol to 8-phenylpropanal O-oxide proceeds with modest stereoselectivity; addition of a tertiary alcohol proceeds with higher selectivity. Product stereochemistry, which is confirmed by conversion of a functionalized hydroperoxy acetal to a 1,2-dioxane, is found to derive from nucleophilic attack through a Felkin-Anh type transition state. Trapping of a carbonyl oxide containing a neighboring hydrogen bond donor proceeds with modest selectivity for both syn- and anti-carbonyl oxide isomers. Ozonolysis of a 3-(trialkylstannyl)-1-enol ether proceeds with loss of the stannyl-bearing carbon through the possible intermediacy of a vinyl peroxide.< |
| Doi | 10.1021/jo00130a021 |
| Wosid | WOS:A1995TK91900021 |
| Is Certified Translation | No |
| Dupe Override | No |
| Comments | Source: Web of Science A1995TK91900021 |
| Is Public | Yes |
| Is Qa | No |