Functionalization of N-[(silyl)methyl]-β-lactam carbanions with carbon electrophiles

Journal of Organic Chemistry

Volumn 71, Issue 17, 2006, Pages 6368-6373

  Palomo, Claudio ^a   Aizpurua, Jesus M ^a   Benito, Ana ^a   Cuerdo, Lourdes ^a   Fratila, Raluca M ^a   Miranda, José I ^a   Linden, Anthony ^b  

^a UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

^b UNIVERSITY OF ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

CARBANIONS; CARBON ELECTROPHILES; DEPROTONATION;

CARBON; MOLECULAR STRUCTURE; NITROGEN; SILICON;

ORGANIC COMPOUNDS;

BETA LACTAM DERIVATIVE; CARBON; LITHIUM; NITROGEN;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; GEOMETRY; PEPTIDE SYNTHESIS; TEMPERATURE;

ALKYLATION; AMINATION; BETA-LACTAMS; CARBON; CARBON DIOXIDE; CRYSTALLOGRAPHY, X-RAY; LITHIUM COMPOUNDS; METHYLATION; MODELS, MOLECULAR; MOLECULAR STRUCTURE;

EID: 33747385331     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo060537g     Document Type: Article

References (40)

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31. Additional deprotonation trials conducted with several butyllithium/TMEDA combinations at temperatures up to -30 °C provided no evidence of carbanion formation. Above this temperature, only decomposition of compound 12 was observed.
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35. We previously described the α′-carbamoilation of 11 with trimethylsilyl isocyanate, see ref 9a.
36. Spontaneous desilylation of α-trimethylsilyl-carbonyl compounds under acidic aqueous workup conditions is a well-established process. See, for example, the following: Landais, Y. α-Silyl Carbonyl Compounds. In Science of Synthesis: Houben-Weyl, Methods of Molecular Transformations; Fleming, I., Ed.; Thieme: Stuttgart-New York, 2002; Vol. 4, p 757-772.
37. An alternative four-step transformation of N-[bis(trimethylsilyl)-methyl] -β-lactams into N-(carboxymethyl)-β-lactams was developed previously in our laboratory, involving Ce(IV)-promoted degradation of bis-(trimethylsilyl) methyl group and N-alkylation of intermediate NH-β-lactams with benzyl iodoacetate (see ref 9). For a related approach to α-alkyl-N- carboxymethyl-γ-lactams, see the following: Raghavan, B.; Johnson, R. L. J. Org. Chem. 2006, 71, 2151-2154.
38. 2O electrophile also gave α′-methylated β-lactam 19 as the only reaction product, instead of the expected N-[(tert-butoxycarbonyl) methyl]-β-lactam.
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40. The crystallographic data for structures 10 and 13 have previously been deposited at the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-113859 and 132758, respectively, in connection with refs 9b and 9a.