Stereoselective rearrangement of β-hydroxy-N-acyloxazolidin-2-ones to afford N-2-hydroxyethyl-1,3-oxazinane-2,4-diones

Synlett

Volumn , Issue 7, 2005, Pages 1090-1094

  Feuillet, Fred J P ^a   Niyadurupola, D Gangani ^a   Green, Rachel ^a   Cheeseman, Matt ^a   Bull, Steven D ^a  

^a University of Bath Claverton Down   (United Kingdom)

Author keywords

1,3 Oxazinane 2,4 dione; Aldol reaction; Diastereoselective; Intramolecular rearrangement; Zinc alkoxide

Indexed keywords

BETA HYDROXY N ACYLOXAZOLIDIN 2 ONE DERIVATIVE; N2 HYDROXYETHYL 1,3 OXAZINANE 2,4 DIONE DERIVATIVE; OXAZINE DERIVATIVE; OXAZOLIDINONE DERIVATIVE; UNCLASSIFIED DRUG;

ALDOL REACTION; CONFERENCE PAPER; DIASTEREOISOMER; MOLECULAR INTERACTION; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 18744393478     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-865212     Document Type: Conference Paper

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36. 4) and concentrated in vacuo to afford the appropriate syn-aldol which was then purified by chromatography.
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39. 4), and concentrated in vacuo to afford the desired syn-1,3-oxazinane-2,4-dione which was then purified by chromatography.
40. (5,6) coupling constants of >10.0 Hz; see ref. 13c, 14, 16.
41. An alternative mechanism involving zinc alkoxide-catalysed epimerisation of the α-stereocentres of syn-β-aryl-aldols 9i-l (or syn-β-aryl-1,3-oxazinane-2,4-diones 10i-l) was discounted because their acidities are similar to those of the α-stereocentres of syn-β-alkyl-aldols 9a-k that had been shown to rearrange with no loss of stereocontrol under these conditions.
42. A similar reversible retro-aldol/aldol mechanism has been proposed to explain the diastereoselectivity observed for reaction of metal enolates of N-acyl-oxazolidin-2-ones with ketones, see:Bartroli, J.; Turmo, E.; Belloc, J.; Forn, J. J. Org. Chem. 1995, 60, 3000.
43. N-Acyl-oxazolidin-2-one-anti-aldol 15 was prepared using Evans' magnesium halide-catalysed protocol, see ref. 12.
44. -1.