AN EFFICIENT ENANTIOMERIC 3 STEP SYNTHESIS OF BETA-AMINO ACIDS (ESTERS)

Ethyl tributylstannylacetate was reacted with (R)-2-aryl or alkyl-1,3-oxazolidines 6 under very specific (ZnCl2/Et2O.BF3, 0.5 equiv each) Lewis Acid catalyzed conditions to yield (1R, 1'R)-N-2'-hydroxy-1'-phenylethyl-1-aryl or alkyl-2-carboethoxyethylamine 8 in 91-99% de. The amino al...

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Bibliographic Details
Published inTetrahedron letters Vol. 34; no. 1; pp. 47 - 50
Main Authors MOKHALLALATI, MK, WU, MJ, PRIDGEN, LN
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 01.01.1993
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
LITHIUM AMIDE
PHENETHYLAMINES
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Summary:Ethyl tributylstannylacetate was reacted with (R)-2-aryl or alkyl-1,3-oxazolidines 6 under very specific (ZnCl2/Et2O.BF3, 0.5 equiv each) Lewis Acid catalyzed conditions to yield (1R, 1'R)-N-2'-hydroxy-1'-phenylethyl-1-aryl or alkyl-2-carboethoxyethylamine 8 in 91-99% de. The amino alcohol products 8 were converted to aromatic and aliphatic beta-amino esters 9, useful precursors to beta-lactams.
ISSN:0040-4039
DOI:10.1016/S0040-4039(00)60054-0