Catalytic sulfur ylide reactions: Use of diazoacetamides for the diastereoselective synthesis of glycidic amides

Tetrahedron Letters

Volumn 39, Issue 46, 1998, Pages 8517-8520

  Aggarwal, Varinder K ^a   Blackburn, Paul ^a   Fieldhouse, Robin ^b   Jones, Ray V H ^b  

^a UNIVERSITY OF SHEFFIELD   (United Kingdom)

^b ASTRAZENECA   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAMIDE DERIVATIVE; ALDEHYDE; EPOXIDE; GLYCIDOL; GLYCINE DERIVATIVE; SULFUR DERIVATIVE;

CATALYSIS; OXIDATION; REVIEW; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032512017     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01852-8     Document Type: Article

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24. 24) Diazoacetamides were prepared from the corresponding acetoacetamides using the procedure reported by Regitz, substituting 2-naphthylsulfonyl azide for tosyl azide. Regitz, M.; Hocker, J.; Liedhegener, A. Organic Syntheses Coll. Vol. V 1973, 179-182. (formula presented)
25. 2 (13 mg, 5 mol%) were placed in MeCN (0.2 mL) and warmed to 60 °C. The diazoacetamide (1.5 mmol) was dissolved in MeCN (0.5 mL) and added over 3 hours via a syringe pump. After complete addition the reaction was stirred for 1 hour before purification by flash column chromatography.