High stereocontrol in aldol reaction with ketones: Enantioselective synthesis of β-hydroxy γ-ketoesters by ester enolate aldol reactions with 2-acyl-2-alkyl-1,3-dithiane 1-oxides

Journal of Organic Chemistry

Volumn 65, Issue 19, 2000, Pages 6027-6034

  García Ruano, José L ^a   Barros, David ^a   Maestro, M Carmen ^a   Slawin, Alexandra M Z ^b   Bulman Page, Philip C ^b  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

^b LOUGHBOROUGH UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

BETA HYDROXY GAMMA KETOESTER; DIKETONE; ESTER DERIVATIVE; LACTONE DERIVATIVE; LITHIUM DERIVATIVE; SULFOXIDE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DIASTEREOISOMER; ENANTIOMER; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0034703425     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo000494i     Document Type: Article

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66. Major propanoate adducts are also obtained in diastereoisomerically pure form by column chromatography on silica gel.
67. 1Bu.
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71. 3 was necessary in order to achieve complete separation of signals corresponding to the ester ethoxy group.
72. The author has deposited atomic coordinates for this structure with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.
73. For clarity in the discussion we have adopted the numbering indicated from Schemes 1 and 2 (C-2, C-3 and C-4 for the α-position, hydroxylic and dithiane carbon atoms respectively). Numbering in the Experimental Section is according to the correct compound name.
74. 1H NMR signal corresponding to the OH signal in major aldol isomers from reactions with propanoate appears at higher field than that for minor isomers (Δδ ≃ 0.3 ppm), whereas the shift of H-1′ (hydrogen alpha to the ester) of the minor isomers appears at higher field (Δδ ≃ 0.1-0.4 ppm). This trend is reversed for the OH signal in the case of lactone adducts, where the OH signal appears at higher field for the major isomer.