Highly diastereoselective synthesis of 1,2-amino alcohols via nucleophilic addition of organocerium reagents to 4- and 5-oxazolidinonecarbaldehydes

1998 ◽  
Vol 76 (7) ◽  
pp. 1070-1081 ◽  
Author(s):  
Andrew GH Wee ◽  
Fuxing Tang
Keyword(s):  
Nucleophilic Addition ◽  
Amino Alcohols ◽  
Diastereoselective Synthesis

The reaction of chiral, non-racemic 4- and 5-oxazolidinonecarbaldehydes, 6 and 13, with organocerium reagents proceeds efficiently with good to excellent diastereoselectivity to give syn and anti alcohols, respectively. A model to explain the observed diastereoselectivity of the reaction of 6 and 13 is provided. The utility of this method for the synthesis of amino alcohols is exemplified by the synthesis of C-18-D-ribo-phytosphingosine from the anti alcohol 14f.Key words: oxazolidinonecarbaldehydes, organocerium, diastereoselective, amino alcohols, C-18-ribo-phytospingosine.

scholarly journals Applications of tert-butanesulfinamide in the asymmetric synthesis of amines

2003 ◽  
Vol 75 (1) ◽  
pp. 39-46 ◽  
Author(s):  
J. A. Ellman
Keyword(s):  
Amino Acids ◽  
Asymmetric Synthesis ◽  
Nucleophilic Addition ◽  
Amino Alcohols ◽  
Wide Range ◽  
Aldehydes And Ketones ◽  
Directing Group ◽  
High Yields ◽  
Direct Condensation

tert-Butanesulfinamide is prepared using catalytic enantioselective methods in two steps from the extremely inexpensive oil waste by-product, tert-butyl disulfide. Direct condensation of tert-butanesulfinamide with aldehydes and ketones provides tert-butanesulfinyl imines in uniformly high yields. The tert-butanesulfinyl group activates the imines for the addition of many different classes of nucleophiles, serves as a powerful chiral directing group, and after nucleophilic addition is readily cleaved by treatment with acid. A wide range of highly enantioenriched amines, including α-branched and α,α-dibranched amines, α- and β-amino acids, 1,2 and 1,3-amino alcohols and α-trifluoromethyl amines are efficiently synthesized using this methodology.

Diastereoselective synthesis of unsaturated vicinal amino alcohols via Diels-Alder reactions of N-sulfinyl dienophiles

1984 ◽  
Vol 106 (25) ◽  
pp. 7861-7867 ◽  
Author(s):  
Ravi S. Garigipati ◽  
Alan J. Freyer ◽  
Robert R. Whittle ◽  
Steven M. Weinreb
Keyword(s):  
Amino Alcohols ◽  
Diels Alder ◽  
Diastereoselective Synthesis
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