Control of product distribution in the domino metathesis reactions of N-alkynyl 2-azabicyclo[2.2.1]hept-5-en-3-ones. A convenient synthesis of functionalized γ-lactams and indolizidinones

Tetrahedron Letters

Volumn 45, Issue 3, 2004, Pages 565-567

  Arjona, Odón ^a   Csákÿ, Aurelio G ^a   León, Vanessa ^a   Medel, Rocío ^a   Plumet, Joaquín ^a  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

Author keywords

Azabicyclic; Indolizidinones; Lactams; Metathesis

Indexed keywords

BICYCLO COMPOUND; ETHYLENE; GAMMA LACTAM DERIVATIVE; HALIDE; INDOLIZIDINE DERIVATIVE; RUTHENIUM;

ARTICLE; CATALYST; CHELATION; MOLECULAR STABILITY; RING CLOSING METATHESIS; RING OPENING METATHESIS POLYMERIZATION; SYNTHESIS;

EID: 0347624536     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.10.197     Document Type: Article

References (38)

1. The alkene metathesis reaction is one of the most valuable synthetic tools in organic chemistry today and an impressive amount of literature has been devoted to this topic. From 2003 the following general reviews should be considered: Connon S.J., Blechert S. Angew. Chem., Int. Ed. 42:2003;1900 (b) Grubbs R.H., Trnka T.M., Sanford M.S. Fundam. Mol. Catal. 3:2003;187 (c) Soderberg B.C.G. Coord. Chem. Rev. 241:2003;147. In a general context, the seminal comprehensive review of Fürstner A. Angew. Chem., Int. Ed. 39:2000;3012. should also be considered.
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4. The alkene metathesis reaction is one of the most valuable synthetic tools in organic chemistry today and an impressive amount of literature has been devoted to this topic. From 2003 the following general reviews should be considered: Connon S.J., Blechert S. Angew. Chem., Int. Ed. 42:2003;1900 (b) Grubbs R.H., Trnka T.M., Sanford M.S. Fundam. Mol. Catal. 3:2003;187 (c) Soderberg B.C.G. Coord. Chem. Rev. 241:2003;147. In a general context, the seminal comprehensive review of Fürstner A. Angew. Chem., Int. Ed. 39:2000;3012. should also be considered.
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25. For an isolated case in the 7-oxanorbornene series, see Ref. [4b]. A description of the process can be found in Ref. [2a], p 619.
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28. Compound (+)-4 is commercially available in optically pure form. All compounds described herein were synthesized using (+)-4 as starting material.
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30. We recognise implicitly the Chauvin's well known mechanism for metathesis reactions: Herisson J.L., Chauvin Y. Macromol. Chem. 141:1971;161. For a full discussion see Ref. [1d], p 3018 and references cited therein.
31. See, for instance: Banti D., North M. Tetrahedron Lett. 43:2002;1561. See also Ref. 11.
32. Catalyst B has proven of superior activity than A in CM processes. See Ref. [1a].
33. For a general review on the synthesis of nitrogen containing compounds by RCM, including the indolizidine ring system, see: Phillips A.J., Abell A.D. Aldrichim. Acta. 32:1999;75 (a) For more recent references on the synthesis of the indolizidine ring system by RCM, see for instance: Zaminer J., Stapper C., Blechert S. Tetrahedron Lett. 43:2002;6739 (b) Groaning M.D., Meyers A.I. Chem. Comm. 2000;1027 (c) Voigtmann U., Blechert S. Synthesis. 2000;893.
34. For a general review on the synthesis of nitrogen containing compounds by RCM, including the indolizidine ring system, see: Phillips A.J., Abell A.D. Aldrichim. Acta. 32:1999;75 (a) For more recent references on the synthesis of the indolizidine ring system by RCM, see for instance: Zaminer J., Stapper C., Blechert S. Tetrahedron Lett. 43:2002;6739 (b) Groaning M.D., Meyers A.I. Chem. Comm. 2000;1027 (c) Voigtmann U., Blechert S. Synthesis. 2000;893.
35. For a general review on the synthesis of nitrogen containing compounds by RCM, including the indolizidine ring system, see: Phillips A.J., Abell A.D. Aldrichim. Acta. 32:1999;75 (a) For more recent references on the synthesis of the indolizidine ring system by RCM, see for instance: Zaminer J., Stapper C., Blechert S. Tetrahedron Lett. 43:2002;6739 (b) Groaning M.D., Meyers A.I. Chem. Comm. 2000;1027 (c) Voigtmann U., Blechert S. Synthesis. 2000;893.
36. For a general review on the synthesis of nitrogen containing compounds by RCM, including the indolizidine ring system, see: Phillips A.J., Abell A.D. Aldrichim. Acta. 32:1999;75 (a) For more recent references on the synthesis of the indolizidine ring system by RCM, see for instance: Zaminer J., Stapper C., Blechert S. Tetrahedron Lett. 43:2002;6739 (b) Groaning M.D., Meyers A.I. Chem. Comm. 2000;1027 (c) Voigtmann U., Blechert S. Synthesis. 2000;893.
37. (a) See, for instance: Ref. [1d], p 3033 (b) Wallace D.J. Tetrahedron Lett. 44:2003;2145. and references cited therein.
38. All new compounds showed spectroscopic and analytical data consistent with the assigned structures.