Applications of aziridinium ions. Selective syntheses of α,β-diamino esters, α-sulfanyl-β-amino esters, β-lactams, and 1,5-benzodiazepin-2-one

Organic Letters

Volumn 2, Issue 23, 2000, Pages 3555-3557

  Chuang, Tsung Hsun ^a   Sharpless, K Barry ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,5 BENZODIAZEPIN 2 ONE; 1,5-BENZODIAZEPIN-2-ONE; AMINE; AZIRIDINE DERIVATIVE; BENZODIAZEPINE DERIVATIVE; BETA LACTAM; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; ESTER;

ARTICLE; CHEMISTRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; SYNTHESIS;

AMINES; AZIRIDINES; BENZODIAZEPINES; BETA-LACTAMS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; ESTERS; INDICATORS AND REAGENTS;

EID: 0034676536     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol000221+     Document Type: Article

References (30)

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18. According to the general procedure for preparation of the chloroamino ester 4a in refs 3 and 4, 4b, 4c, and 4d were obtained with melting points of 82-84, 50-51, and 79-80°C, respectively (see Supporting Information for spectral data).
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20. 2/hexane or ether gave regioisomerically pure samples of 5a, 5b, 5c, 5f, 5h, 5i, 5j, 5k, 5l, 5q, and 5r with melting points of 69-70, 241-242, 97-99, 122-123, 114-115, 63-65, 118-119, 71-73, 42-44, 112-114, and 87-89°C, respectively (see Supporting Information for spectral data on all products). Although only performed here on a 1.0 mmol scale, these nucleophilic/aziridinium substitutions have proven equally reliable on a 13 g scale.
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25. 4, and concentrated. The residue was filtered through a short plug of silica gel (2 cm in a pipet). which was washed with 10 mL of EtOAc. The combined filtrates were concentrated to give azetidin-2-one 24a (80.0 mg, 88%) with a melting point of 86-88°C. As described for 24a, 24b (an oil) and 24c (nip 78-80°C) were obtained in 90% and 99% yields, respectively (see Supporting Information for spectral data on all products).
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30. The reaction was performed successfully on a 2 g scale.