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Synthesis of 3-aryl-3-pyrrolines and 3-arylpyrroles via spontaneous rearrangement of N-sulfinyl 2-aryl-2-vinylaziridines

(2011) SYNLETT. p.674-678
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Abstract
Addition of vinylmagnesium bromide across chiral achloro N-tert-butanesulfinyl ketimines afforded 3-aryl-1-(tert-butanesulfinyl)-3-pyrrolines in high yield (65–91%) after purification by means of recrystallization from diethyl ether. The synthesis of these 3-aryl-3-pyrrolines is explained by initial formation of 2-aryl-2-vinylaziridines which spontaneously rearrange via carbon–nitrogen bond cleavage to form stabilized 1,3-dipolar intermediates which in turn ring closed to 3-pyrrolines.
Keywords
TERT-BUTANESULFINYL IMINES, pyrrolines, MONOAMINE-OXIDASE-B, 4+1 PYRROLINE ANNULATION, BOVINE PLASMA AMINE, ASYMMETRIC-SYNTHESIS, CHIRAL AZIRIDINES, STEREOSELECTIVE-SYNTHESIS, VINYL AZIRIDINES, SUBSTITUTED AZIRIDINES, CLOSING METATHESIS, imines, heterocycles, rearrangement, aziridines

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Citation

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Chicago
Leemans, Erika , Filip Colpaert, Sven Mangelinckx, Stijn De Brabandere, Bram Denolf, and Norbert De Kimpe. 2011. “Synthesis of 3-aryl-3-pyrrolines and 3-arylpyrroles via Spontaneous Rearrangement of N-sulfinyl 2-aryl-2-vinylaziridines.” Synlett (5): 674–678.
APA
Leemans, E., Colpaert, F., Mangelinckx, S., De Brabandere, S., Denolf, B., & De Kimpe, N. (2011). Synthesis of 3-aryl-3-pyrrolines and 3-arylpyrroles via spontaneous rearrangement of N-sulfinyl 2-aryl-2-vinylaziridines. SYNLETT, (5), 674–678.
Vancouver
1.
Leemans E, Colpaert F, Mangelinckx S, De Brabandere S, Denolf B, De Kimpe N. Synthesis of 3-aryl-3-pyrrolines and 3-arylpyrroles via spontaneous rearrangement of N-sulfinyl 2-aryl-2-vinylaziridines. SYNLETT. 2011;(5):674–8.
MLA
Leemans, Erika , Filip Colpaert, Sven Mangelinckx, et al. “Synthesis of 3-aryl-3-pyrrolines and 3-arylpyrroles via Spontaneous Rearrangement of N-sulfinyl 2-aryl-2-vinylaziridines.” SYNLETT 5 (2011): 674–678. Print.
@article{1205901,
  abstract     = {Addition of vinylmagnesium bromide across chiral achloro
N-tert-butanesulfinyl ketimines afforded 3-aryl-1-(tert-butanesulfinyl)-3-pyrrolines in high yield (65--91\%) after purification by means of recrystallization from diethyl ether. The synthesis of these 3-aryl-3-pyrrolines is explained by initial formation of 2-aryl-2-vinylaziridines which spontaneously rearrange via carbon--nitrogen bond cleavage to form stabilized 1,3-dipolar intermediates which in turn ring closed to 3-pyrrolines.},
  author       = {Leemans, Erika  and Colpaert, Filip and Mangelinckx, Sven and De Brabandere, Stijn and Denolf, Bram  and De Kimpe, Norbert},
  issn         = {0936-5214},
  journal      = {SYNLETT},
  keyword      = {TERT-BUTANESULFINYL IMINES,pyrrolines,MONOAMINE-OXIDASE-B,4+1 PYRROLINE ANNULATION,BOVINE PLASMA AMINE,ASYMMETRIC-SYNTHESIS,CHIRAL AZIRIDINES,STEREOSELECTIVE-SYNTHESIS,VINYL AZIRIDINES,SUBSTITUTED AZIRIDINES,CLOSING METATHESIS,imines,heterocycles,rearrangement,aziridines},
  language     = {eng},
  number       = {5},
  pages        = {674--678},
  title        = {Synthesis of 3-aryl-3-pyrrolines and 3-arylpyrroles via spontaneous rearrangement of N-sulfinyl 2-aryl-2-vinylaziridines},
  url          = {http://dx.doi.org/10.1055/s-0030-1259554},
  year         = {2011},
}

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