New aspects of the indium chemistry of carbonyl-β-lactams

Synthesis

Volumn , Issue 8, 2003, Pages 1163-1170

  Alcaide, Benito ^a   Almendros, Pedro ^b   Aragoncillo, Cristina ^a   Rodríguez Acebes, Raquel ^a  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

^b INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

Author keywords

Addition reactions; Asymmetric synthesis; Indium; Lactams; Organometallic reagents

Indexed keywords

REACTION KINETICS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

REGIOCHEMISTRY;

INDIUM;

BETA LACTAM DERIVATIVE; CARBONYL DERIVATIVE; INDIUM; ORGANIC COMPOUND; REAGENT;

ADDITION REACTION; AQUEOUS SOLUTION; ARTICLE; ASYMMETRIC SYNTHESIS; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONFORMATIONAL TRANSITION; MOLECULAR STABILITY; OPTICAL ROTATION; ORGANIC CHEMISTRY; REACTION ANALYSIS; STEREOCHEMISTRY; SUBSTITUTION REACTION;

EID: 0038387935     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-39388     Document Type: Article

References (31)

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13. See, for instance: (a) Alcaide, B.; Almendros, P. Synlett 2002, 381. (b) Alcaide, B.; Almendros, P. Chem. Soc. Rev. 2001, 30, 226. (c) Palomo, C.; Aizpurua, J. M.; Ganboa, I.; Oiarbide, M. Synlett 2001, 1813. (d) Palomo, C.; Aizpurua, J. M.; Ganboa, I.; Oiarbide, M. Amino Acids 1999, 16, 321. (e) Ojima, I.; Delaloge, F. Chem. Soc. Rev. 1997, 26, 377. (f) Manhas, M. S.; Wagle, D. R.; Chiang, J.; Bose, A. K. Heterocycles 1988, 27, 1755.
14. See, for instance: (a) Alcaide, B.; Almendros, P. Synlett 2002, 381. (b) Alcaide, B.; Almendros, P. Chem. Soc. Rev. 2001, 30, 226. (c) Palomo, C.; Aizpurua, J. M.; Ganboa, I.; Oiarbide, M. Synlett 2001, 1813. (d) Palomo, C.; Aizpurua, J. M.; Ganboa, I.; Oiarbide, M. Amino Acids 1999, 16, 321. (e) Ojima, I.; Delaloge, F. Chem. Soc. Rev. 1997, 26, 377. (f) Manhas, M. S.; Wagle, D. R.; Chiang, J.; Bose, A. K. Heterocycles 1988, 27, 1755.
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23. For recent selected reviews on organic reaction in aq media, see: (a) Lindström, U. M. Chem. Rev. 2002, 102, 2751. (b) Manabe, K.; Kobayashi, S. Chem.-Eur. J. 2002, 8, 4095. (c) Paquette, L. A. In Green Chemistry: Frontiers in Benign Chemical Synthesis and Processing; Anastas, P. T.; Williamson, T. C., Eds.; Oxford University Press: New York, 1998. (d) Lubineau, A.; Augé, J. Top. Curr. Chem. 1999, 206, 1.
24. For recent selected reviews on organic reaction in aq media, see: (a) Lindström, U. M. Chem. Rev. 2002, 102, 2751. (b) Manabe, K.; Kobayashi, S. Chem.-Eur. J. 2002, 8, 4095. (c) Paquette, L. A. In Green Chemistry: Frontiers in Benign Chemical Synthesis and Processing; Anastas, P. T.; Williamson, T. C., Eds.; Oxford University Press: New York, 1998. (d) Lubineau, A.; Augé, J. Top. Curr. Chem. 1999, 206, 1.
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26. Similar results were obtained using zinc instead of indium, see: (a) Alcaide, B.; Almendros, P.; Aragoncillo, C.; Rodríguez-Acebes, R. J. Org. Chem. 2001, 66, 5208. (b) Alcaide, B.; Almendros, P.; Aragoncillo, C. Org. Lett. 2000, 2, 1411.
27. Similar results were obtained using zinc instead of indium, see: (a) Alcaide, B.; Almendros, P.; Aragoncillo, C.; Rodríguez-Acebes, R. J. Org. Chem. 2001, 66, 5208. (b) Alcaide, B.; Almendros, P.; Aragoncillo, C. Org. Lett. 2000, 2, 1411.
28. 11
29. The zinc-mediated reaction afforded the syn-adducts with complete regioselectivity and good diastereoselectivity, see: Alcaide, B.; Almendros, P.; Aragoncillo, C. Chem.-Eur. J. 2002, 8, 1719.
30. When the above coupling was promoted by zinc, the yield fell considerably, see: Alcaide, B.; Almendros, P.; Rodríguez-Acebes, R. J. Org. Chem. 2002, 67, 1925.
31. Chan has postulated that an allylindium(I) intermediate is formed in indium-mediated organometallic reactions in aqueous media, see: Chan, T. H.; Yang, Y. J. Am. Chem. Soc. 1999, 121, 3228.