219697-84-4Relevant academic research and scientific papers
Highly diastereoselective synthesis of 1,2-amino alcohols via nucleophilic addition of organocerium reagents to 4- and 5- oxazolidinonecarbaldehydes
Wee, Andrew G. H.,Tang, Fuxing
, p. 1070 - 1081 (2007/10/03)
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.
Diastereoselectivity in the addition of organocerium reagents to 4- and 5-oxazolidonecarbaldehydes: Synthesis of syn- and anti-alcohols
Wee, Andrew G. H.,Tang, Fuxing
, p. 6677 - 6680 (2007/10/03)
Chiral non-racemic 4- and 5-oxazolidonecarbaldehydes, typified by 2 and 7, react highly diastereoselectively with organocerium reagents to give moderate to good yields of syn- and anti-alcohols, respectively. Rationalizations for the observed diastereoselectivites are presented. The synthetic potential of this method is exemplified by the synthesis of C-18-D-ribo-phytosphingosine which was obtained as its tetraacetate.
