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Volumn , Issue 18, 2007, Pages 2879-2881

Direct synthesis of substituted vinyl aziridines

Author keywords

Aziridine; Imine; Sulfonium; Vinyl; Ylide

Indexed keywords

ALLYLTETRAHYDROTHIPHENIUM SALT; AZIRIDINE DERIVATIVE; N (DIMETHYLSULFAMOYL)PHENYLIMINE; UNCLASSIFIED DRUG; VINYL AZIRIDINE;

ARTICLE; ASYMMETRIC SYNTHESIS; CHEMICAL STRUCTURE; LABORATORY;

EID: 36549044325 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2007-990956 Document Type: Article

Times cited : (15)

References (20)

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20
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- Typical Procedure for 1-(2′-Dimethylamine-2′-sulfonyl)-2- phenyl-3-vinylaziridine (2a) Vacuum-dried sulfonium salt 1a (0.61 g, 2 equiv, 4.73 mmol) in DMSO, 15 mL) was stirred under argon. N-(Dimethylsulfamoyl)phenylimine (0.48 g, 1 equiv, 2.26 mmol) in DMSO (8 mL) was added to the solution followed by LiOt-Bu, 0.38 g, 2 equiv, 4.45 mmol, and the progress of the reaction was monitored by TLC (25% EtOAc-PE, After 10 min the reaction was judged to be complete and was quenched with ice-cold brine, filtered through a pad of Celite and washed with Et 2O. The resultant bilayer was separated and the aqueous layer was extracted with Et2O, the combined organic extracts were dried over anhyd Na2SO4, filtered, and concentrated under vacuum. Purification by flash column chromatography on neutral alumina, eluting with 5% EtOAc-PE, furnished 0.39 g, 66, as a 2:1 mixture of trans/cis diastereomers. The sep
- 3): δ = 137.1, 136.0, 133.8, 129.1, 128.9, 128.4, 128.2, 127.6, 127.1, 121.9, 48.0, 46.2, 39.0.

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