A novel rearrangement of N-propargyl vinylaziridines. Mechanistic diversity in the aza-[2,3]-Wittig rearrangement

Tetrahedron Letters

Volumn 37, Issue 14, 1996, Pages 2495-2498

  Åhman, Jens ^a   Somfai, Peter ^a  

^a LUND INSTITUTE OF TECHNOLOGY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

AZIRIDINE DERIVATIVE; PYRIDINE DERIVATIVE; PYRROLINE DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029916446     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00302-4     Document Type: Article

References (19)

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3. Åhman, J.; Somfai, P. Tetrahedron 1995, 51, 9747.
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6. b) Nakai, T.; Mikami, K. Chem. Rev. 1986, 86, 885.
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11. Åhman, J.; Somfai, P. Synth. Commun. 1994, 24, 1121.
12. For a discussion of nitrogen-stabilized carbanions, see: Gawley, R. E.; Rein, K. in Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I. Eds.; Pergamon: Oxford, 1991; Vol. 3, Chapter 3.11.
13. 26NSi (M+H): 236.1835, found: 236.1839.
14. n-BuLi and n-BuLi/TMEDA are also effective in this deprotonation and gives an identical product composition compared to s-BuLi.
15. For some preparations of 2-unsubstituted-3-alkylidene-1-pyrrolines, see: a) Helak, B.; Karsten, E.; Spengler, K.; Tressl, R.; Rewicki, D. J. Agric. Food Chem. 1989, 37, 405.
16. b) Nomura, Y.; Bando, T.; Takeuchi, Y.; Tomuda, S. Bull. Chem. Soc. Jpn. 1983, 56, 3199.
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