Stereoselective synthesis of 1,4-dideoxy-1,4-imino-d-allitol and formal synthesis of (2S,3R,4S)-3,4-dihydroxyproline |
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| Authors: | A MadhanB Venkateswara Rao |
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| Institution: | Organic Division III, Indian Institute of Chemical Technology, Hyderabad 500007, India |
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| Abstract: | A stereoselective synthesis of 1,4-dideoxy-1,4-imino-d-allitol 1 and formal synthesis of (2S,3R,4S)-3,4-dihydroxyproline was achieved via the addition of vinylmagnesium bromide to the benzylimine derived from (R)-2,3-O-isopropylidene glyceraldehyde followed by N-allylation, ring-closing metathesis (RCM), and dihydroxylation. |
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| Keywords: | imine Grignard reaction N-allylation ring-closing metathesis dihydroxylation azasugars |
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