Reductive cyclisation of azidolactams with Bu3P/LiAlH 4

Synthesis

Volumn , Issue 3, 2005, Pages 475-479

  Nandra, Gurdeep S ^a   Porter, Michael J ^a   Elliott, Jason M ^b  

^a UNIVERSITY COLLEGE LONDON   (United Kingdom)

^b NEUROSCIENCE RESEARCH CENTRE   (United Kingdom)

Author keywords

Aminals; Azides; Bicyclic Compounds; Heterocycles; Lactams

Indexed keywords

LITHIUM COMPOUNDS; NITROGEN COMPOUNDS; REDUCTION;

AZIDOLACTAMS; OCTAHYDROPYRROLO[2,3-B]PYRROLES; REDUCTIVE CYCLIZATION; TRI-N-BUTYLPHOSPHINE;

SYNTHESIS (CHEMICAL);

ALUMINUM DERIVATIVE; AZIDOLACTAM DERIVATIVE; HETEROCYCLIC COMPOUND; LACTAM DERIVATIVE; LITHIUM DERIVATIVE; OCTAHYDROPYRROLO[2,3 B]PYRROLE; PHOSPHINE DERIVATIVE; PHOSPHORUS; PYRROLE DERIVATIVE; TRI N BUTYLPHOSPHINE; UNCLASSIFIED DRUG;

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

EID: 14644410441     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-837292     Document Type: Article

References (9)

1. Thorsett, E. D.; Harris, E. E.; Patchett, A. A. J. Org. Chem. 1978, 43, 4276.
2. Daoust, B.; Lessard, J. Tetrahedron 1999, 55, 3495.
3. Masamune, S.; Kaiho, T.; Garvey, D. S. J. Am. Chem. Soc. 1982, 104, 5521.
4. 2O; see: Gololobov, Y. G.; Zhmurova, I. N.; Kasukhin, L. F. Tetrahedron 1981, 37, 437.
5. Red-Al® has previously been used for the reductive cyclisation of azido-oxindoles: Overman, L. E.; Paone, D. V. J. Am. Chem. Soc. 2001, 123, 9465.
6. Thorsett et al. (ref.1) report a coupling constant of 7 Hz between the ring junction protons in a cis-fused octahydro[2,3-b]pyrrole.
7. Coates, B.; Montgomery, D. J.; Stevenson, P. J. Tetrahedron 1994, 50, 4025.
8. Abdel-Baky, S.; Giese, R. W. J. Org. Chem. 1986, 51, 3390.
9. The relative stereochemistry of this compound is assigned by analogy to reactions in ref.7