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Fine-Tuned Aminal Cleavage: A Concise Route to Differentially Protected Enantiopure syn-α,β-Diamino Esters.
- Source :
-
Journal of Organic Chemistry . 3/5/2004, Vol. 69 Issue 5, p1542-1547. 6p. 3 Diagrams, 2 Charts. - Publication Year :
- 2004
-
Abstract
- A survey of routes for aminal cleavage of N-sulfinylimidazolidines has been carried out, and selective conditions to cleave the aminal moiety while preserving the sulfinamide group unaltered have been found. Thus, the treatment of enantiopure N-sulfinylimidazolidines with aqueous H3PO4 in THF affords enantiopure N-sulfinyldiamino esters in excellent yields, while the presence of MeOH as cosolvent allows for the simultaneous removal of the sulfinamide group and aminal cleavage. The behavior of these substrates in a variety of chemical transformations has been explored. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 00223263
- Volume :
- 69
- Issue :
- 5
- Database :
- Academic Search Index
- Journal :
- Journal of Organic Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 12732681
- Full Text :
- https://doi.org/10.1021/jo035613j