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Highly stereoselective syntheses of syn- and anti-1,2-amino alcohols.
MedLine Citation:
PMID:  11846643     Owner:  NLM     Status:  PubMed-not-MEDLINE    
Abstract/OtherAbstract:
The reduction of N-protected amino ketones can be carried stereoselectively to produce either the syn- or anti-amino alcohol diastereomer. Carbamate-protected amino ketones can be reduced predictably and selectively to anti-amino alcohols with LiAlH(O-t-Bu)3 in ethanol at -78 degrees C. N-Trityl-protected amino ketones can be reduced selectively to syn-amino alcohols with LiAlH(O-t-Bu)3 in THF at -5 degrees C.
Authors:
Robert V Hoffman; Najib Maslouh; Francisco Cervantes-Lee
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  67     ISSN:  0022-3263     ISO Abbreviation:  J. Org. Chem.     Publication Date:  2002 Feb 
Date Detail:
Created Date:  2002-02-15     Completed Date:  2002-05-20     Revised Date:  2003-11-03    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  1045-56     Citation Subset:  -    
Affiliation:
Department of Chemistry and Biochemistry, North Horseshoe Drive, New Mexico State University, Las Cruces, New Mexico 88003-8001, USA. rhoffman@nmsu.edu
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