Journal article
Synthesis of gamma-amino esters via Mn-mediated radical addition to chiral gamma-hydrazonoesters
Organic letters, Vol.11(5), pp.1095-1098
03/05/2009
DOI: 10.1021/ol802932v
PMID: 19199819
Abstract
Highly stereoselective Mn-mediated couplings of alkyl iodides with chiral N-acylhydrazones bearing ester functionality afford a series of gamma-hydrazino esters, including gamma-substituted, alpha,gamma-disubstituted, and alpha,alpha,gamma-trisubstituted examples. In contrast to prior work with chiral N-acylhydrazones, high stereoselectivity was observed even in the absence of Lewis acid. Microwave-assisted acylation with trifluoroacetic anhydride and reductive N-N bond cleavage provided the gamma-amino ester functionality in a synthetically useful N-TFA-protected form.
Details
- Title: Subtitle
- Synthesis of gamma-amino esters via Mn-mediated radical addition to chiral gamma-hydrazonoesters
- Creators
- Gregory K Friestad - Department of Chemistry, University of Iowa, Iowa City, Iowa 52242, USA. gregory-friestad@uiowa.eduKoushik Banerjee
- Resource Type
- Journal article
- Publication Details
- Organic letters, Vol.11(5), pp.1095-1098
- Publisher
- United States
- DOI
- 10.1021/ol802932v
- PMID
- 19199819
- ISSN
- 1523-7060
- eISSN
- 1523-7052
- Language
- English
- Date published
- 03/05/2009
- Academic Unit
- Chemistry
- Record Identifier
- 9983985972602771
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