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 2-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.
Original language | English (US) |
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Pages (from-to) | 8218-8222 |
Number of pages | 5 |
Journal | Journal of Organic Chemistry |
Volume | 60 |
Issue number | 25 |
DOIs | |
State | Published - Dec 1 1995 |
ASJC Scopus subject areas
- Organic Chemistry