Diastereoselective alkylations of oxazolidinone glycolates: A useful extension of the Evans asymmetric alkylation

Authors
Crimmins, MT Emmitte, KA Katz, JD
Citation
Mt. Crimmins et al., Diastereoselective alkylations of oxazolidinone glycolates: A useful extension of the Evans asymmetric alkylation, ORG LETT, 2(14), 2000, pp. 2165-2167
Citations number
31
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
2
Issue
14
Year of publication
2000
Pages
2165 - 2167
Database
ISI
SICI code
1523-7060(20000713)2:14<2165:DAOOGA>2.0.ZU;2-8
Abstract
[GRAPHICS] The diastereoselective alkylation of glycolate oxazolidinones has been demo nstrated as a method for the enantioselective preparation of alpha-alkoxy c arboxylic acid derivatives and selectively protected 1,2-diols, Various pro tecting groups on the glycolate hydroxyl and multiple substitution patterns on allylic iodides are tolerated in the alkylation, Yields for the alkylat ions are typically 70-85% with diastereoselectivities of >98:2.