Journal article
3-fluoro-6-tert-butyltetrahydropyranosyl trichloroacetamidates. "chiral auxiliary donors" for hydroxyalkyl radicals
Organic letters, Vol.6(8), pp.1217-1219
04/15/2004
Handle:
https://hdl.handle.net/2376/114632
PMID: 15070301
Abstract
An improved THP-based chiral auxiliary for hydroxyalkyl radicals is reported. The key modifications involve introduction of a fluorine substituent at C-3 to make the acetal center more robust and the use of Schmidt's trichloroacetamidate glycosylation methodology for efficient attachment of the auxiliary to the radical precursor. The resulting chiral hydroxyalkyl radical equivalents add to methyl 2-trifluoroacetoxyacrylate with selectivities ranging from 9:1 (0 degrees C) to 15:1 (-78 degrees C). [structure: see text]
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Details
- Title
- 3-fluoro-6-tert-butyltetrahydropyranosyl trichloroacetamidates. "chiral auxiliary donors" for hydroxyalkyl radicals
- Creators
- Philip Garner - Department of Chemistry, Case Western Reserve University, Cleveland, OH 44106-7078, USA. ppg@case.eduOzge Seşenoğlu
- Publication Details
- Organic letters, Vol.6(8), pp.1217-1219
- Academic Unit
- Chemistry, Department of
- Publisher
- United States
- Identifiers
- 99900547885201842
- Language
- English
- Resource Type
- Journal article