Synthesis of enantiopure 4-(dihydroxyalkyl)-β-lactams from D-mannitol using Ley's BDA-protected L-glyceraldehyde

Synlett

Volumn , Issue 20, 2007, Pages 3180-3182

  Areces, Pilar ^a   Carrasco, Esther ^a   Light, Mark E ^b   Santos, Miguel ^a   Plumet, Joaquín ^c  

^a UNIVERSITY OF EXTREMADURA   (Spain)

^b UNIVERSITY OF SOUTHAMPTON   (United Kingdom)

^c UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

Author keywords

lactams; Chiral auxiliaries; Protected glyceraldehydes; Staudinger reaction; Stereoselective synthesis

Indexed keywords

BETA LACTAM; ETHYLENE GLYCOL; GLYCERALDEHYDE IMINE DERIVATIVE; IMINE; MANNITOL; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DEPROTECTION REACTION; ENANTIOMER; PROTON NUCLEAR MAGNETIC RESONANCE; STAUDINGER REACTION; STEREOCHEMISTRY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 37749051888     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-992375     Document Type: Article

References (20)

1. For selected reviews on the use of 1,2-diacetals as chiral building blocks in organic synthesis, see: (a) Ley, S. V.; Baeschlin, D. K.; Dixon, D. J.; Foster, A. C.; Ince, S. J.; Priepke, H. W. M.; Reynolds, D. J. Chem. Rev. 2001, 101, 53.
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3. (c) Ley, S. V.; Polara, A. J. Org. Chem. 2007, 72, 5943.
4. Ley, S. V.; Michel, P. Synthesis 2004, 147.
5. Both enantiomers of glyceraldehyde acetonide are prone to racemization and rapid polymerization. See: (a) Hubschwerlen, J.; Specklin, L.; Higelin, J. Org. Synth 1995, 72, 1.
6. (b) Schmid, C. R.; Bryant, J. D. Org. Synth. 1995, 72, 6.
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16. 2O (1.6 mL) at 0°C was treated with the corresponding amine (0.681 mmol) and molecular sieves (Merck 4 Å). After the reaction was complete, the molecular sieves were filtered and the solvent was evaporated under vacuum to yield the corresponding imine 3. Compound 3a: R = Bn; reaction time: 25 min, 0°C, 98%. Compound 3b: R = (R)-CH(Me)(Ph); reaction time: 15 min, 0°C, 99%. Compound 3c: R = (S)-CH(Me)(Ph); reaction time: 15 min, 0°C, 81%.
17. 1 = PhO; reaction time: 15 min, r.t., 61%.
18. -1. Crystallographic data (excluding structure factors) for compound 4g have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 661976.
19. 3): δ = 166.1 (CO), 157.4 (Ph), 141.0 (Ph), 129.7, 128.9, 127.8, 127.0 (Ph), 122.7 (Ph), 115.9 (Ph), 79.5 (C-3), 71.2 (C-1′), 63.6 (C-2′), 59.5 (C-1″), 54.7 (C-4), 20.3 (Me).
20. 3): δ = 165.8 (CO), 155.6 (Ph), 134.9 (Ph), 129.6, 129.0, 128.3, 128.2 (Ph), 117.4 (Ph), 81.4 (C-3), 70.8 (C-1′), 63.9 (C-2′), 57.4 (C-4), 45.5 (C-1″).