192815-75-1Relevant academic research and scientific papers
Cycloadditions of chiral carbonyl ylides with imine dipolarophiles as a route to enantiomerically pure α-amino-β-hydroxy acids
Gan, Yu,Harwood, Laurence M.,Richards, Simon C.,Smith, Ian E.D.,Vinader, Victoria
body text, p. 723 - 725 (2009/09/25)
The preparation of enantiomerically pure threo-β-amino-α-hydroxy acids via 1,3-dipolar cycloadditions of imine dipolarophiles with the chiral isomuenchnone derived from (5R)-5-phenylmorpholin-3-one 1 is described. The cycloadducts were obtained with excellent diastereofacial- and exo-selectivity. Subsequent hydrolysis and chemoselective exocyclic amide cleavage afforded the threo-β-amino-α-hydroxy acids with recovery of the initial chiral auxiliary.
Cycloadditions of 1,3-oxazolium-4-olates (Isomunchnones) by Rhodium(II)-Induced decomposition of α-Diazocarbonyl derivatives of (5R)- and (5S)-phenyloxazin-3-one as a chiral template
Angell, Richard,Fengler-Veith, Marion,Finch, Harry,Harwood, Laurence M.,Tucker, Toby T.
, p. 4517 - 4520 (2007/10/03)
Cycloadducts (6-9) were synthesised from isomunchnone derivatives of (5R)- and (5S)-phenyloxazin-3-one by rhodium(II)-catalysed decomposition of α-diazocompounds (3a-c). Additions to various carbon-carbon dipolarophiles proceeded with high endo/exo-selectivities and moderate diastereofacial selectivities.
