Highly stereocontrolled synthesis of a novel tribactam by reaction of an ester enolate with a N-trimethylsilylimine

Tetrahedron Letters

Volumn 37, Issue 14, 1996, Pages 2467-2470

  Camerini, Roberto ^a   Panunzio, Mauro ^a   Bonanomi, Giorgio ^b   Donati, Daniele ^b   Perboni, Alcide ^b  

^a CNR   (Italy)

^b GSK   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBIOTIC AGENT; AZETIDINONE DERIVATIVE; TRIBACTAM DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029967487     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00394-2     Document Type: Article

References (37)

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32. The synthesis of azetidin-2-one 9 was carried out in the following way. To a stirred solution of aldehyde 6 (100mmol) in THF (300 ml) was added dropwise, at -78°C, a solution of LiHMDSA in THF (100 ml, 1 M solution, Aldrich). The solution was stirred for 1 hr at r.t., then a previous prepared solution of lithium tert-buthoxy acetate (400 mmoles), prepared at -78° C from LiHMDSA and tert-buthoxy acetate, was added. The mixture was stirred for 8 hr while the temperature reached spontaneously r.t. The reaction was quenched with saturated ammonium chloride solution. After usual work-up, the oily product was treated with ether to give pure crystalline 9 (55%).
33. 3): -4.38, -4.96, 17.89, 19.57, 22.72, 25.07, 26.59, 31.84, 35.91, 49.94, 58.88, 66.32, 82.56, 164.25. Exact mass: 368.261690 (Calc. 368.262098).
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