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Azabicyclo[3.1.0]hexane-1-ols as frameworks for the asymmetric synthesis of biologically active compounds
- Source :
-
Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry . Dec2007, Vol. 48 Issue 49, p8765-8767. 3p. - Publication Year :
- 2007
-
Abstract
- Abstract: Azabicyclo[3.1.0]hexane-1-ols, easily obtained by Ti(IV)-mediated cyclopropanation of amino acid derivatives, constitute versatile, and unprecedented intermediates for the asymmetric synthesis of pharmacologically active products. Indeed, through selective rearrangement, these compounds undergo unusual ring cleavage to lead to pyrrolidinones. Fe(III)-promoted ring opening followed by basic dehydrohalogenation furnishes optically active dihydropyridinones, while Ce(IV)-promoted ring opening provides chiral tricyclopiperidinones via a radical process. [Copyright &y& Elsevier]
- Subjects :
- *ORGANIC acids
*AMINO acids
*PHARMACOLOGY
*BIOACTIVE compounds
Subjects
Details
- Language :
- English
- ISSN :
- 00404039
- Volume :
- 48
- Issue :
- 49
- Database :
- Academic Search Index
- Journal :
- Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 27626174
- Full Text :
- https://doi.org/10.1016/j.tetlet.2007.10.003