- Regio- and stereoselective opening of oxiranes through neighbouring group participation: Stereocontrolled synthesis of enantiopure hydroxylated oxazolidin-2-ones
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The regio- and stereo-selective ring opening of (S)-pyroglutaminol derived epoxides provides an effective route to protected syn,syn-aminodiol units. The procedure involves the chemoselective aminolysis or alcoholysis of (3R,4R,5R)-N-(tert-butoxycarbonyl)-3,4-epoxy-5-[(1- ethoxy)ethoxymethyl]pyrrolidin-2-one (10), followed by the formation in quantitative yield of oxazolidinone intermediates, through the mediation of neighbouring N-Boc groups. The practical synthetic interest of this route is illustrated by the example of (3R,4S,5R)-3,4-diacetoxy-5- (acetoxymethyl)pyrrolidin-2-one which should serve as useful building block in further syntheses.
- Langlois, Nicole,Moro, Alberto
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p. 3483 - 3488
(2007/10/03)
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- Enantioselective Synthesis of (S)-5-Aminopiperidin-2-one from (S)-Pyroglutaminol
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(5S)-5-aminopiperidin-2-one and several derivatives were synthesized from (S)-pyroglutaminol through ring opening and Mitsunobu reaction as the key steps.
- Panday, Sharad Kumar,Langlois, Nicole
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p. 8205 - 8208
(2007/10/02)
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