A convenient route to N-alkyl-2-tributylstannyl-pyrrolidines involving reductive amination

Tetrahedron Letters

Volumn 41, Issue 13, 2000, Pages 2235-2237

  Ashweek, Neil J ^a   Coldham, Iain ^a   Vennall, Graham P ^a  

^a UNIVERSITY OF EXETER   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

PYRROLIDINE DERIVATIVE;

AMINATION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; REACTION ANALYSIS; REDUCTION; SYNTHESIS;

EID: 0034719888     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00137-4     Document Type: Article

References (11)

1. Quench with external electrophiles: (a) Burchat, A. F.; Chong, J. M.; Park, S. B. Tetrahedron Lett. 1993, 34, 51; (b) Gawley, R. E.; Zhang, Q. J. Org. Chem. 1995, 60, 5763.
2. Quench with external electrophiles: (a) Burchat, A. F.; Chong, J. M.; Park, S. B. Tetrahedron Lett. 1993, 34, 51; (b) Gawley, R. E.; Zhang, Q. J. Org. Chem. 1995, 60, 5763.
3. 2,3-Sigmatropic rearrangement: (a) Coldham, I. J. Chem. Soc., Perkin Trans. 1 1993, 1275; (b) Gawley, R. E.; Zhang, Q.; Campagna, S. J. Am. Chem. Soc. 1995, 117, 11 817.
4. 2,3-Sigmatropic rearrangement: (a) Coldham, I. J. Chem. Soc., Perkin Trans. 1 1993, 1275; (b) Gawley, R. E.; Zhang, Q.; Campagna, S. J. Am. Chem. Soc. 1995, 117, 11 817.
5. Anionic cyclizations: (a) Coldham, I.; Fernàndez, J.-C.; Snowden, D. J. Tetrahedron Lett. 1999, 40, 1819; (b) Coldham, I.; Hufton, R. Tetrahedron 1996, 52, 12541.
6. Anionic cyclizations: (a) Coldham, I.; Fernàndez, J.-C.; Snowden, D. J. Tetrahedron Lett. 1999, 40, 1819; (b) Coldham, I.; Hufton, R. Tetrahedron 1996, 52, 12541.
7. Beak, P.; Kerrick, S. T.; Wu, S.; Chu, J. J. Am. Chem. Soc. 1994, 116, 3231.
8. Boeckman, R. K.; Potenza, J. C. Tetrahedron Lett. 1985, 26, 1411.
9. Coldham, I.; Hufton, R.; Snowden, D. J. J. Am. Chem. Soc. 1996, 118, 5322.
10. 3CN (126 mg, 2.0 mmol) and 4-pentenal (92 mg, 1.1 mmol) were added and after 15 min the reaction was absorbed onto basic alumina. Chromatography (basic alumina, 10% EtOAc/pet.) gave the stannane 4d (143 mg, 0.33 mmol, 62%) as an oil.
11. 3), respectively.