Highly diastereoselective [3+2] cycloadditions between nonracemic p-tolylsulfinimines and iminoesters: An efficient entry to enantiopure imidazolidines and vicinal diaminoalcohols

Chemistry - A European Journal

Volumn 9, Issue 12, 2003, Pages 2867-2876

  Viso, Alma ^a   De la Pradilla, Roberto Fernández ^a   García, Ana ^a   Guerrero Strachan, Carlos ^a   Alonso, Marta ^a   Tortosa, Mariola ^a   Flores, Aida ^a   Martínez Ripoll, Martín ^b   Fonseca, Isabel ^b   André, Isabelle ^b   Rodrígue, Ana ^c  

^a INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

^b INSTITUTO DE QUÍMICA FÍSICA ROCASOLANO   (Spain)

^c UNIVERSITY OF CASTILLA LA MANCHA   (Spain)

Author keywords

Cycloadditions; Heterocycles; Imidazolidines sulfinimines; Ylides

Indexed keywords

ALCOHOLS; LITHIUM COMPOUNDS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

CYCLOADDITIONS;

ESTERS;

4 TOLYLSULFINIMINE; ALUMINUM DERIVATIVE; AMINOALCOHOL; AZOMETHINE YLIDE; ESTER; HYDROGEN; IMIDAZOLIDINE DERIVATIVE; IMINE; IMINOESTER; LEWIS ACID; LITHIUM DERIVATIVE; N SULFINYL N' BENZYL DIAMINOALCOHOL; N SULFINYLIMIDAZOLIDINE; SULFUR DERIVATIVE; TOLUENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CYCLOADDITION; DIASTEREOISOMER; HYDROLYSIS; OXIDATION; REACTION ANALYSIS; REDUCTION; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0038789210     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200204674     Document Type: Article

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28. Vicinal diamines are important chiral auxiliaries. For an excellent review, see: a) D. Lucet, T. Le Gall, C. Mioskowski, Angew. Chem. 1998, 110, 2724-2772; Angew. Chem. Int. Ed. 1998, 37, 2580-2627; for recent leading references, see: b) F. Eustache, P. I. Dalko, J. Cossy, Org. Lett. 2002, 4, 1263-1265; c) S. Kobayashi, T. Hamada, K. Manabe, J. Am. Chem. Soc. 2002,124, 5640-5641; d) P. O'Brien, T. D. Towers, J. Org. Chem. 2002, 67, 304-307; e) K. R. Knudsen, T. I Risgaard, N. Nishiwaki, K. V. Gothelf, K. A. Jørgensen, J. Am. Chem. Soc. 2001, 123, 5843-5844; f) G. Li, H. -X. Wei, S. H. Kim, M. D. Carducci, Angew. Chem. 2001, 113, 4407-4410; Angew. Chem. Int. Ed. 2001, 40, 4277-4280; g) N. Nishiwaki, K. R. Knudsen, K. V. Gothelf, K. A. Jørgensen, Angew. Chem. 2001, 113, 3080-3083; Angew. Chem. Int. Ed. 2001, 40, 2992-2995; h) I. Coldham, R. C. B. Copley, T. F. N. Haxell, S. Howard, Org. Lett. 2001, 3, 3799-3801; i) A. Alexakis, A.-S. Chauvin, R. Stouvenel, E. Vrancken, S. Mutti, P. Mangeney, Tetrahedron: Asymmetry 2001, 12, 1171-1178; j) S. Demay, A. Kotschy, P. Knochel, Synthesis 2001, 863-866.
29. Vicinal diamines are important chiral auxiliaries. For an excellent review, see: a) D. Lucet, T. Le Gall, C. Mioskowski, Angew. Chem. 1998, 110, 2724-2772; Angew. Chem. Int. Ed. 1998, 37, 2580-2627; for recent leading references, see: b) F. Eustache, P. I. Dalko, J. Cossy, Org. Lett. 2002, 4, 1263-1265; c) S. Kobayashi, T. Hamada, K. Manabe, J. Am. Chem. Soc. 2002,124, 5640-5641; d) P. O'Brien, T. D. Towers, J. Org. Chem. 2002, 67, 304-307; e) K. R. Knudsen, T. I Risgaard, N. Nishiwaki, K. V. Gothelf, K. A. Jørgensen, J. Am. Chem. Soc. 2001, 123, 5843-5844; f) G. Li, H. -X. Wei, S. H. Kim, M. D. Carducci, Angew. Chem. 2001, 113, 4407-4410; Angew. Chem. Int. Ed. 2001, 40, 4277-4280; g) N. Nishiwaki, K. R. Knudsen, K. V. Gothelf, K. A. Jørgensen, Angew. Chem. 2001, 113, 3080-3083; Angew. Chem. Int. Ed. 2001, 40, 2992-2995; h) I. Coldham, R. C. B. Copley, T. F. N. Haxell, S. Howard, Org. Lett. 2001, 3, 3799-3801; i) A. Alexakis, A.-S. Chauvin, R. Stouvenel, E. Vrancken, S. Mutti, P. Mangeney, Tetrahedron: Asymmetry 2001, 12, 1171-1178; j) S. Demay, A. Kotschy, P. Knochel, Synthesis 2001, 863-866.
30. Vicinal diamines are important chiral auxiliaries. For an excellent review, see: a) D. Lucet, T. Le Gall, C. Mioskowski, Angew. Chem. 1998, 110, 2724-2772; Angew. Chem. Int. Ed. 1998, 37, 2580-2627; for recent leading references, see: b) F. Eustache, P. I. Dalko, J. Cossy, Org. Lett. 2002, 4, 1263-1265; c) S. Kobayashi, T. Hamada, K. Manabe, J. Am. Chem. Soc. 2002,124, 5640-5641; d) P. O'Brien, T. D. Towers, J. Org. Chem. 2002, 67, 304-307; e) K. R. Knudsen, T. I Risgaard, N. Nishiwaki, K. V. Gothelf, K. A. Jørgensen, J. Am. Chem. Soc. 2001, 123, 5843-5844; f) G. Li, H. -X. Wei, S. H. Kim, M. D. Carducci, Angew. Chem. 2001, 113, 4407-4410; Angew. Chem. Int. Ed. 2001, 40, 4277-4280; g) N. Nishiwaki, K. R. Knudsen, K. V. Gothelf, K. A. Jørgensen, Angew. Chem. 2001, 113, 3080-3083; Angew. Chem. Int. Ed. 2001, 40, 2992-2995; h) I. Coldham, R. C. B. Copley, T. F. N. Haxell, S. Howard, Org. Lett. 2001, 3, 3799-3801; i) A. Alexakis, A.-S. Chauvin, R. Stouvenel, E. Vrancken, S. Mutti, P. Mangeney, Tetrahedron: Asymmetry 2001, 12, 1171-1178; j) S. Demay, A. Kotschy, P. Knochel, Synthesis 2001, 863-866.
31. Vicinal diamines are important chiral auxiliaries. For an excellent review, see: a) D. Lucet, T. Le Gall, C. Mioskowski, Angew. Chem. 1998, 110, 2724-2772; Angew. Chem. Int. Ed. 1998, 37, 2580-2627; for recent leading references, see: b) F. Eustache, P. I. Dalko, J. Cossy, Org. Lett. 2002, 4, 1263-1265; c) S. Kobayashi, T. Hamada, K. Manabe, J. Am. Chem. Soc. 2002,124, 5640-5641; d) P. O'Brien, T. D. Towers, J. Org. Chem. 2002, 67, 304-307; e) K. R. Knudsen, T. I Risgaard, N. Nishiwaki, K. V. Gothelf, K. A. Jørgensen, J. Am. Chem. Soc. 2001, 123, 5843-5844; f) G. Li, H. -X. Wei, S. H. Kim, M. D. Carducci, Angew. Chem. 2001, 113, 4407-4410; Angew. Chem. Int. Ed. 2001, 40, 4277-4280; g) N. Nishiwaki, K. R. Knudsen, K. V. Gothelf, K. A. Jørgensen, Angew. Chem. 2001, 113, 3080-3083; Angew. Chem. Int. Ed. 2001, 40, 2992-2995; h) I. Coldham, R. C. B. Copley, T. F. N. Haxell, S. Howard, Org. Lett. 2001, 3, 3799-3801; i) A. Alexakis, A.-S. Chauvin, R. Stouvenel, E. Vrancken, S. Mutti, P. Mangeney, Tetrahedron: Asymmetry 2001, 12, 1171-1178; j) S. Demay, A. Kotschy, P. Knochel, Synthesis 2001, 863-866.
32. Vicinal diamines are important chiral auxiliaries. For an excellent review, see: a) D. Lucet, T. Le Gall, C. Mioskowski, Angew. Chem. 1998, 110, 2724-2772; Angew. Chem. Int. Ed. 1998, 37, 2580-2627; for recent leading references, see: b) F. Eustache, P. I. Dalko, J. Cossy, Org. Lett. 2002, 4, 1263-1265; c) S. Kobayashi, T. Hamada, K. Manabe, J. Am. Chem. Soc. 2002,124, 5640-5641; d) P. O'Brien, T. D. Towers, J. Org. Chem. 2002, 67, 304-307; e) K. R. Knudsen, T. I Risgaard, N. Nishiwaki, K. V. Gothelf, K. A. Jørgensen, J. Am. Chem. Soc. 2001, 123, 5843-5844; f) G. Li, H. -X. Wei, S. H. Kim, M. D. Carducci, Angew. Chem. 2001, 113, 4407-4410; Angew. Chem. Int. Ed. 2001, 40, 4277-4280; g) N. Nishiwaki, K. R. Knudsen, K. V. Gothelf, K. A. Jørgensen, Angew. Chem. 2001, 113, 3080-3083; Angew. Chem. Int. Ed. 2001, 40, 2992-2995; h) I. Coldham, R. C. B. Copley, T. F. N. Haxell, S. Howard, Org. Lett. 2001, 3, 3799-3801; i) A. Alexakis, A.-S. Chauvin, R. Stouvenel, E. Vrancken, S. Mutti, P. Mangeney, Tetrahedron: Asymmetry 2001, 12, 1171-1178; j) S. Demay, A. Kotschy, P. Knochel, Synthesis 2001, 863-866.
33. Vicinal diamines are important chiral auxiliaries. For an excellent review, see: a) D. Lucet, T. Le Gall, C. Mioskowski, Angew. Chem. 1998, 110, 2724-2772; Angew. Chem. Int. Ed. 1998, 37, 2580-2627; for recent leading references, see: b) F. Eustache, P. I. Dalko, J. Cossy, Org. Lett. 2002, 4, 1263-1265; c) S. Kobayashi, T. Hamada, K. Manabe, J. Am. Chem. Soc. 2002,124, 5640-5641; d) P. O'Brien, T. D. Towers, J. Org. Chem. 2002, 67, 304-307; e) K. R. Knudsen, T. I Risgaard, N. Nishiwaki, K. V. Gothelf, K. A. Jørgensen, J. Am. Chem. Soc. 2001, 123, 5843-5844; f) G. Li, H. -X. Wei, S. H. Kim, M. D. Carducci, Angew. Chem. 2001, 113, 4407-4410; Angew. Chem. Int. Ed. 2001, 40, 4277-4280; g) N. Nishiwaki, K. R. Knudsen, K. V. Gothelf, K. A. Jørgensen, Angew. Chem. 2001, 113, 3080-3083; Angew. Chem. Int. Ed. 2001, 40, 2992-2995; h) I. Coldham, R. C. B. Copley, T. F. N. Haxell, S. Howard, Org. Lett. 2001, 3, 3799-3801; i) A. Alexakis, A.-S. Chauvin, R. Stouvenel, E. Vrancken, S. Mutti, P. Mangeney, Tetrahedron: Asymmetry 2001, 12, 1171-1178; j) S. Demay, A. Kotschy, P. Knochel, Synthesis 2001, 863-866.
34. Vicinal diamines are important chiral auxiliaries. For an excellent review, see: a) D. Lucet, T. Le Gall, C. Mioskowski, Angew. Chem. 1998, 110, 2724-2772; Angew. Chem. Int. Ed. 1998, 37, 2580-2627; for recent leading references, see: b) F. Eustache, P. I. Dalko, J. Cossy, Org. Lett. 2002, 4, 1263-1265; c) S. Kobayashi, T. Hamada, K. Manabe, J. Am. Chem. Soc. 2002,124, 5640-5641; d) P. O'Brien, T. D. Towers, J. Org. Chem. 2002, 67, 304-307; e) K. R. Knudsen, T. I Risgaard, N. Nishiwaki, K. V. Gothelf, K. A. Jørgensen, J. Am. Chem. Soc. 2001, 123, 5843-5844; f) G. Li, H. -X. Wei, S. H. Kim, M. D. Carducci, Angew. Chem. 2001, 113, 4407-4410; Angew. Chem. Int. Ed. 2001, 40, 4277-4280; g) N. Nishiwaki, K. R. Knudsen, K. V. Gothelf, K. A. Jørgensen, Angew. Chem. 2001, 113, 3080-3083; Angew. Chem. Int. Ed. 2001, 40, 2992-2995; h) I. Coldham, R. C. B. Copley, T. F. N. Haxell, S. Howard, Org. Lett. 2001, 3, 3799-3801; i) A. Alexakis, A.-S. Chauvin, R. Stouvenel, E. Vrancken, S. Mutti, P. Mangeney, Tetrahedron: Asymmetry 2001, 12, 1171-1178; j) S. Demay, A. Kotschy, P. Knochel, Synthesis 2001, 863-866.
35. Vicinal diamines are important chiral auxiliaries. For an excellent review, see: a) D. Lucet, T. Le Gall, C. Mioskowski, Angew. Chem. 1998, 110, 2724-2772; Angew. Chem. Int. Ed. 1998, 37, 2580-2627; for recent leading references, see: b) F. Eustache, P. I. Dalko, J. Cossy, Org. Lett. 2002, 4, 1263-1265; c) S. Kobayashi, T. Hamada, K. Manabe, J. Am. Chem. Soc. 2002,124, 5640-5641; d) P. O'Brien, T. D. Towers, J. Org. Chem. 2002, 67, 304-307; e) K. R. Knudsen, T. I Risgaard, N. Nishiwaki, K. V. Gothelf, K. A. Jørgensen, J. Am. Chem. Soc. 2001, 123, 5843-5844; f) G. Li, H. -X. Wei, S. H. Kim, M. D. Carducci, Angew. Chem. 2001, 113, 4407-4410; Angew. Chem. Int. Ed. 2001, 40, 4277-4280; g) N. Nishiwaki, K. R. Knudsen, K. V. Gothelf, K. A. Jørgensen, Angew. Chem. 2001, 113, 3080-3083; Angew. Chem. Int. Ed. 2001, 40, 2992-2995; h) I. Coldham, R. C. B. Copley, T. F. N. Haxell, S. Howard, Org. Lett. 2001, 3, 3799-3801; i) A. Alexakis, A.-S. Chauvin, R. Stouvenel, E. Vrancken, S. Mutti, P. Mangeney, Tetrahedron: Asymmetry 2001, 12, 1171-1178; j) S. Demay, A. Kotschy, P. Knochel, Synthesis 2001, 863-866.
36. Vicinal diamines are important chiral auxiliaries. For an excellent review, see: a) D. Lucet, T. Le Gall, C. Mioskowski, Angew. Chem. 1998, 110, 2724-2772; Angew. Chem. Int. Ed. 1998, 37, 2580-2627; for recent leading references, see: b) F. Eustache, P. I. Dalko, J. Cossy, Org. Lett. 2002, 4, 1263-1265; c) S. Kobayashi, T. Hamada, K. Manabe, J. Am. Chem. Soc. 2002,124, 5640-5641; d) P. O'Brien, T. D. Towers, J. Org. Chem. 2002, 67, 304-307; e) K. R. Knudsen, T. I Risgaard, N. Nishiwaki, K. V. Gothelf, K. A. Jørgensen, J. Am. Chem. Soc. 2001, 123, 5843-5844; f) G. Li, H. -X. Wei, S. H. Kim, M. D. Carducci, Angew. Chem. 2001, 113, 4407-4410; Angew. Chem. Int. Ed. 2001, 40, 4277-4280; g) N. Nishiwaki, K. R. Knudsen, K. V. Gothelf, K. A. Jørgensen, Angew. Chem. 2001, 113, 3080-3083; Angew. Chem. Int. Ed. 2001, 40, 2992-2995; h) I. Coldham, R. C. B. Copley, T. F. N. Haxell, S. Howard, Org. Lett. 2001, 3, 3799-3801; i) A. Alexakis, A.-S. Chauvin, R. Stouvenel, E. Vrancken, S. Mutti, P. Mangeney, Tetrahedron: Asymmetry 2001, 12, 1171-1178; j) S. Demay, A. Kotschy, P. Knochel, Synthesis 2001, 863-866.
37. Vicinal diamines are important chiral auxiliaries. For an excellent review, see: a) D. Lucet, T. Le Gall, C. Mioskowski, Angew. Chem. 1998, 110, 2724-2772; Angew. Chem. Int. Ed. 1998, 37, 2580-2627; for recent leading references, see: b) F. Eustache, P. I. Dalko, J. Cossy, Org. Lett. 2002, 4, 1263-1265; c) S. Kobayashi, T. Hamada, K. Manabe, J. Am. Chem. Soc. 2002,124, 5640-5641; d) P. O'Brien, T. D. Towers, J. Org. Chem. 2002, 67, 304-307; e) K. R. Knudsen, T. I Risgaard, N. Nishiwaki, K. V. Gothelf, K. A. Jørgensen, J. Am. Chem. Soc. 2001, 123, 5843-5844; f) G. Li, H. -X. Wei, S. H. Kim, M. D. Carducci, Angew. Chem. 2001, 113, 4407-4410; Angew. Chem. Int. Ed. 2001, 40, 4277-4280; g) N. Nishiwaki, K. R. Knudsen, K. V. Gothelf, K. A. Jørgensen, Angew. Chem. 2001, 113, 3080-3083; Angew. Chem. Int. Ed. 2001, 40, 2992-2995; h) I. Coldham, R. C. B. Copley, T. F. N. Haxell, S. Howard, Org. Lett. 2001, 3, 3799-3801; i) A. Alexakis, A.-S. Chauvin, R. Stouvenel, E. Vrancken, S. Mutti, P. Mangeney, Tetrahedron: Asymmetry 2001, 12, 1171-1178; j) S. Demay, A. Kotschy, P. Knochel, Synthesis 2001, 863-866.
38. Vicinal diamines are important chiral auxiliaries. For an excellent review, see: a) D. Lucet, T. Le Gall, C. Mioskowski, Angew. Chem. 1998, 110, 2724-2772; Angew. Chem. Int. Ed. 1998, 37, 2580-2627; for recent leading references, see: b) F. Eustache, P. I. Dalko, J. Cossy, Org. Lett. 2002, 4, 1263-1265; c) S. Kobayashi, T. Hamada, K. Manabe, J. Am. Chem. Soc. 2002,124, 5640-5641; d) P. O'Brien, T. D. Towers, J. Org. Chem. 2002, 67, 304-307; e) K. R. Knudsen, T. I Risgaard, N. Nishiwaki, K. V. Gothelf, K. A. Jørgensen, J. Am. Chem. Soc. 2001, 123, 5843-5844; f) G. Li, H. -X. Wei, S. H. Kim, M. D. Carducci, Angew. Chem. 2001, 113, 4407-4410; Angew. Chem. Int. Ed. 2001, 40, 4277-4280; g) N. Nishiwaki, K. R. Knudsen, K. V. Gothelf, K. A. Jørgensen, Angew. Chem. 2001, 113, 3080-3083; Angew. Chem. Int. Ed. 2001, 40, 2992-2995; h) I. Coldham, R. C. B. Copley, T. F. N. Haxell, S. Howard, Org. Lett. 2001, 3, 3799-3801; i) A. Alexakis, A.-S. Chauvin, R. Stouvenel, E. Vrancken, S. Mutti, P. Mangeney, Tetrahedron: Asymmetry 2001, 12, 1171-1178; j) S. Demay, A. Kotschy, P. Knochel, Synthesis 2001, 863-866.
39. Vicinal diamines are important chiral auxiliaries. For an excellent review, see: a) D. Lucet, T. Le Gall, C. Mioskowski, Angew. Chem. 1998, 110, 2724-2772; Angew. Chem. Int. Ed. 1998, 37, 2580-2627; for recent leading references, see: b) F. Eustache, P. I. Dalko, J. Cossy, Org. Lett. 2002, 4, 1263-1265; c) S. Kobayashi, T. Hamada, K. Manabe, J. Am. Chem. Soc. 2002,124, 5640-5641; d) P. O'Brien, T. D. Towers, J. Org. Chem. 2002, 67, 304-307; e) K. R. Knudsen, T. I Risgaard, N. Nishiwaki, K. V. Gothelf, K. A. Jørgensen, J. Am. Chem. Soc. 2001, 123, 5843-5844; f) G. Li, H. -X. Wei, S. H. Kim, M. D. Carducci, Angew. Chem. 2001, 113, 4407-4410; Angew. Chem. Int. Ed. 2001, 40, 4277-4280; g) N. Nishiwaki, K. R. Knudsen, K. V. Gothelf, K. A. Jørgensen, Angew. Chem. 2001, 113, 3080-3083; Angew. Chem. Int. Ed. 2001, 40, 2992-2995; h) I. Coldham, R. C. B. Copley, T. F. N. Haxell, S. Howard, Org. Lett. 2001, 3, 3799-3801; i) A. Alexakis, A.-S. Chauvin, R. Stouvenel, E. Vrancken, S. Mutti, P. Mangeney, Tetrahedron: Asymmetry 2001, 12, 1171-1178; j) S. Demay, A. Kotschy, P. Knochel, Synthesis 2001, 863-866.
40. For a review on the use of aminals in asymmetric synthesis, see: a) A. Alexakis, P. Mangeney, in Advanced Asymmetric Synthesis (Ed.: G. R. Stephenson), Chapman & Hall, London, 1996, pp. 93-110; for leading references, see: b) J. Clayden, L. W. Lai, Angew. Chem. 1999, 111, 2755-2757; Angew. Chem. Int. Ed. 1999, 38, 2556-2558; c) A. L. Braga, F. Vargas, C. C. Silveira, L. H. de Andrade, Tetrahedron Lett. 2002, 43, 2335-2337; d) A. R. Katritzky, K. Suzuki, H.-Y. He, J. Org. Chem. 2002, 67, 3109-3114; e) A. Alexakis, I. Aujard, J. Pytkowicz, S. Roland, P. Mangeney, J. Chem. Soc. Perkin Trans. 1 2001, 949-951; f) M. E. Jung, A. Huang, Org. Lett. 2000, 2, 2659-2661; g) I. Coldham, P. M. A. Houdayer, R. A. Judkins, D. R. Witty, Synthesis 1998, 1463-1466; h) A. Alexakis, J.-P. Tranchier, N. Lensen, P. Mangeney, J. Am. Chem. Soc. 1995, 117, 10767-10768; i) M.-J. Jin, S.-H. Kim, S.-J. Lee, Y.-M. Kim, Tetrahedron Lett. 2002, 43, 7409-7411.
41. For a review on the use of aminals in asymmetric synthesis, see: a) A. Alexakis, P. Mangeney, in Advanced Asymmetric Synthesis (Ed.: G. R. Stephenson), Chapman & Hall, London, 1996, pp. 93-110; for leading references, see: b) J. Clayden, L. W. Lai, Angew. Chem. 1999, 111, 2755-2757; Angew. Chem. Int. Ed. 1999, 38, 2556-2558; c) A. L. Braga, F. Vargas, C. C. Silveira, L. H. de Andrade, Tetrahedron Lett. 2002, 43, 2335-2337; d) A. R. Katritzky, K. Suzuki, H.-Y. He, J. Org. Chem. 2002, 67, 3109-3114; e) A. Alexakis, I. Aujard, J. Pytkowicz, S. Roland, P. Mangeney, J. Chem. Soc. Perkin Trans. 1 2001, 949-951; f) M. E. Jung, A. Huang, Org. Lett. 2000, 2, 2659-2661; g) I. Coldham, P. M. A. Houdayer, R. A. Judkins, D. R. Witty, Synthesis 1998, 1463-1466; h) A. Alexakis, J.-P. Tranchier, N. Lensen, P. Mangeney, J. Am. Chem. Soc. 1995, 117, 10767-10768; i) M.-J. Jin, S.-H. Kim, S.-J. Lee, Y.-M. Kim, Tetrahedron Lett. 2002, 43, 7409-7411.
42. For a review on the use of aminals in asymmetric synthesis, see: a) A. Alexakis, P. Mangeney, in Advanced Asymmetric Synthesis (Ed.: G. R. Stephenson), Chapman & Hall, London, 1996, pp. 93-110; for leading references, see: b) J. Clayden, L. W. Lai, Angew. Chem. 1999, 111, 2755-2757; Angew. Chem. Int. Ed. 1999, 38, 2556-2558; c) A. L. Braga, F. Vargas, C. C. Silveira, L. H. de Andrade, Tetrahedron Lett. 2002, 43, 2335-2337; d) A. R. Katritzky, K. Suzuki, H.-Y. He, J. Org. Chem. 2002, 67, 3109-3114; e) A. Alexakis, I. Aujard, J. Pytkowicz, S. Roland, P. Mangeney, J. Chem. Soc. Perkin Trans. 1 2001, 949-951; f) M. E. Jung, A. Huang, Org. Lett. 2000, 2, 2659-2661; g) I. Coldham, P. M. A. Houdayer, R. A. Judkins, D. R. Witty, Synthesis 1998, 1463-1466; h) A. Alexakis, J.-P. Tranchier, N. Lensen, P. Mangeney, J. Am. Chem. Soc. 1995, 117, 10767-10768; i) M.-J. Jin, S.-H. Kim, S.-J. Lee, Y.-M. Kim, Tetrahedron Lett. 2002, 43, 7409-7411.
43. For a review on the use of aminals in asymmetric synthesis, see: a) A. Alexakis, P. Mangeney, in Advanced Asymmetric Synthesis (Ed.: G. R. Stephenson), Chapman & Hall, London, 1996, pp. 93-110; for leading references, see: b) J. Clayden, L. W. Lai, Angew. Chem. 1999, 111, 2755-2757; Angew. Chem. Int. Ed. 1999, 38, 2556-2558; c) A. L. Braga, F. Vargas, C. C. Silveira, L. H. de Andrade, Tetrahedron Lett. 2002, 43, 2335-2337; d) A. R. Katritzky, K. Suzuki, H.-Y. He, J. Org. Chem. 2002, 67, 3109-3114; e) A. Alexakis, I. Aujard, J. Pytkowicz, S. Roland, P. Mangeney, J. Chem. Soc. Perkin Trans. 1 2001, 949-951; f) M. E. Jung, A. Huang, Org. Lett. 2000, 2, 2659-2661; g) I. Coldham, P. M. A. Houdayer, R. A. Judkins, D. R. Witty, Synthesis 1998, 1463-1466; h) A. Alexakis, J.-P. Tranchier, N. Lensen, P. Mangeney, J. Am. Chem. Soc. 1995, 117, 10767-10768; i) M.-J. Jin, S.-H. Kim, S.-J. Lee, Y.-M. Kim, Tetrahedron Lett. 2002, 43, 7409-7411.
44. For a review on the use of aminals in asymmetric synthesis, see: a) A. Alexakis, P. Mangeney, in Advanced Asymmetric Synthesis (Ed.: G. R. Stephenson), Chapman & Hall, London, 1996, pp. 93-110; for leading references, see: b) J. Clayden, L. W. Lai, Angew. Chem. 1999, 111, 2755-2757; Angew. Chem. Int. Ed. 1999, 38, 2556-2558; c) A. L. Braga, F. Vargas, C. C. Silveira, L. H. de Andrade, Tetrahedron Lett. 2002, 43, 2335-2337; d) A. R. Katritzky, K. Suzuki, H.-Y. He, J. Org. Chem. 2002, 67, 3109-3114; e) A. Alexakis, I. Aujard, J. Pytkowicz, S. Roland, P. Mangeney, J. Chem. Soc. Perkin Trans. 1 2001, 949-951; f) M. E. Jung, A. Huang, Org. Lett. 2000, 2, 2659-2661; g) I. Coldham, P. M. A. Houdayer, R. A. Judkins, D. R. Witty, Synthesis 1998, 1463-1466; h) A. Alexakis, J.-P. Tranchier, N. Lensen, P. Mangeney, J. Am. Chem. Soc. 1995, 117, 10767-10768; i) M.-J. Jin, S.-H. Kim, S.-J. Lee, Y.-M. Kim, Tetrahedron Lett. 2002, 43, 7409-7411.
45. For a review on the use of aminals in asymmetric synthesis, see: a) A. Alexakis, P. Mangeney, in Advanced Asymmetric Synthesis (Ed.: G. R. Stephenson), Chapman & Hall, London, 1996, pp. 93-110; for leading references, see: b) J. Clayden, L. W. Lai, Angew. Chem. 1999, 111, 2755-2757; Angew. Chem. Int. Ed. 1999, 38, 2556-2558; c) A. L. Braga, F. Vargas, C. C. Silveira, L. H. de Andrade, Tetrahedron Lett. 2002, 43, 2335-2337; d) A. R. Katritzky, K. Suzuki, H.-Y. He, J. Org. Chem. 2002, 67, 3109-3114; e) A. Alexakis, I. Aujard, J. Pytkowicz, S. Roland, P. Mangeney, J. Chem. Soc. Perkin Trans. 1 2001, 949-951; f) M. E. Jung, A. Huang, Org. Lett. 2000, 2, 2659-2661; g) I. Coldham, P. M. A. Houdayer, R. A. Judkins, D. R. Witty, Synthesis 1998, 1463-1466; h) A. Alexakis, J.-P. Tranchier, N. Lensen, P. Mangeney, J. Am. Chem. Soc. 1995, 117, 10767-10768; i) M.-J. Jin, S.-H. Kim, S.-J. Lee, Y.-M. Kim, Tetrahedron Lett. 2002, 43, 7409-7411.
46. For a review on the use of aminals in asymmetric synthesis, see: a) A. Alexakis, P. Mangeney, in Advanced Asymmetric Synthesis (Ed.: G. R. Stephenson), Chapman & Hall, London, 1996, pp. 93-110; for leading references, see: b) J. Clayden, L. W. Lai, Angew. Chem. 1999, 111, 2755-2757; Angew. Chem. Int. Ed. 1999, 38, 2556-2558; c) A. L. Braga, F. Vargas, C. C. Silveira, L. H. de Andrade, Tetrahedron Lett. 2002, 43, 2335-2337; d) A. R. Katritzky, K. Suzuki, H.-Y. He, J. Org. Chem. 2002, 67, 3109-3114; e) A. Alexakis, I. Aujard, J. Pytkowicz, S. Roland, P. Mangeney, J. Chem. Soc. Perkin Trans. 1 2001, 949-951; f) M. E. Jung, A. Huang, Org. Lett. 2000, 2, 2659-2661; g) I. Coldham, P. M. A. Houdayer, R. A. Judkins, D. R. Witty, Synthesis 1998, 1463-1466; h) A. Alexakis, J.-P. Tranchier, N. Lensen, P. Mangeney, J. Am. Chem. Soc. 1995, 117, 10767-10768; i) M.-J. Jin, S.-H. Kim, S.-J. Lee, Y.-M. Kim, Tetrahedron Lett. 2002, 43, 7409-7411.
47. For a review on the use of aminals in asymmetric synthesis, see: a) A. Alexakis, P. Mangeney, in Advanced Asymmetric Synthesis (Ed.: G. R. Stephenson), Chapman & Hall, London, 1996, pp. 93-110; for leading references, see: b) J. Clayden, L. W. Lai, Angew. Chem. 1999, 111, 2755-2757; Angew. Chem. Int. Ed. 1999, 38, 2556-2558; c) A. L. Braga, F. Vargas, C. C. Silveira, L. H. de Andrade, Tetrahedron Lett. 2002, 43, 2335-2337; d) A. R. Katritzky, K. Suzuki, H.-Y. He, J. Org. Chem. 2002, 67, 3109-3114; e) A. Alexakis, I. Aujard, J. Pytkowicz, S. Roland, P. Mangeney, J. Chem. Soc. Perkin Trans. 1 2001, 949-951; f) M. E. Jung, A. Huang, Org. Lett. 2000, 2, 2659-2661; g) I. Coldham, P. M. A. Houdayer, R. A. Judkins, D. R. Witty, Synthesis 1998, 1463-1466; h) A. Alexakis, J.-P. Tranchier, N. Lensen, P. Mangeney, J. Am. Chem. Soc. 1995, 117, 10767-10768; i) M.-J. Jin, S.-H. Kim, S.-J. Lee, Y.-M. Kim, Tetrahedron Lett. 2002, 43, 7409-7411.
48. For a review on the use of aminals in asymmetric synthesis, see: a) A. Alexakis, P. Mangeney, in Advanced Asymmetric Synthesis (Ed.: G. R. Stephenson), Chapman & Hall, London, 1996, pp. 93-110; for leading references, see: b) J. Clayden, L. W. Lai, Angew. Chem. 1999, 111, 2755-2757; Angew. Chem. Int. Ed. 1999, 38, 2556-2558; c) A. L. Braga, F. Vargas, C. C. Silveira, L. H. de Andrade, Tetrahedron Lett. 2002, 43, 2335-2337; d) A. R. Katritzky, K. Suzuki, H.-Y. He, J. Org. Chem. 2002, 67, 3109-3114; e) A. Alexakis, I. Aujard, J. Pytkowicz, S. Roland, P. Mangeney, J. Chem. Soc. Perkin Trans. 1 2001, 949-951; f) M. E. Jung, A. Huang, Org. Lett. 2000, 2, 2659-2661; g) I. Coldham, P. M. A. Houdayer, R. A. Judkins, D. R. Witty, Synthesis 1998, 1463-1466; h) A. Alexakis, J.-P. Tranchier, N. Lensen, P. Mangeney, J. Am. Chem. Soc. 1995, 117, 10767-10768; i) M.-J. Jin, S.-H. Kim, S.-J. Lee, Y.-M. Kim, Tetrahedron Lett. 2002, 43, 7409-7411.
49. For a review on the use of aminals in asymmetric synthesis, see: a) A. Alexakis, P. Mangeney, in Advanced Asymmetric Synthesis (Ed.: G. R. Stephenson), Chapman & Hall, London, 1996, pp. 93-110; for leading references, see: b) J. Clayden, L. W. Lai, Angew. Chem. 1999, 111, 2755-2757; Angew. Chem. Int. Ed. 1999, 38, 2556-2558; c) A. L. Braga, F. Vargas, C. C. Silveira, L. H. de Andrade, Tetrahedron Lett. 2002, 43, 2335-2337; d) A. R. Katritzky, K. Suzuki, H.-Y. He, J. Org. Chem. 2002, 67, 3109-3114; e) A. Alexakis, I. Aujard, J. Pytkowicz, S. Roland, P. Mangeney, J. Chem. Soc. Perkin Trans. 1 2001, 949-951; f) M. E. Jung, A. Huang, Org. Lett. 2000, 2, 2659-2661; g) I. Coldham, P. M. A. Houdayer, R. A. Judkins, D. R. Witty, Synthesis 1998, 1463-1466; h) A. Alexakis, J.-P. Tranchier, N. Lensen, P. Mangeney, J. Am. Chem. Soc. 1995, 117, 10767-10768; i) M.-J. Jin, S.-H. Kim, S.-J. Lee, Y.-M. Kim, Tetrahedron Lett. 2002, 43, 7409-7411.
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61. For a review on applications of sulfinimines, see: a) F. A. Davis, P. Zhou, B.-C. Chen, Chem. Soc. Rev. 1998, 27, 13-18; for recent leading references, see: b) F. A. Davis, K. R. Prasad, P. J. Carroll, J. Org. Chem. 2002, 67, 7802-7806; c) G. K. S. Prakash, M. Mandal, J. Am. Chem. Soc. 2002, 124, 6538-6539; d) B.-F. Li, M.-J. Zhang, X.-L. Hou, L.-X. Dai, J. Org. Chem. 2002, 67, 2902-2906; e) T. Kochi, T. P. Tang, J. A. Ellman, J. Am. Chem. Soc. 2002, 124, 6518-6519; f) V. K. Aggarwal, A. M. Martín Castro, A. Mereu, H. Adams, Tetrahedron Lett. 2002, 43, 1577-1581; g) R. Kumareswaran, A. Hassner, Tetrahedron: Asymmetry 2001, 12, 3409-3415; h) A. Asensio, P. Bravo, M. Crucianelli, A. Farina, S. Fustero, J. García Soler, S. V. Meille, W. Panzeri, F. Viani, A. Volonterio, M. Zanda, Eur. J. Org. Chem. 2001, 1449-1458; i) I. R. Cooper, R. Grigg, W. S. MacLachlan, M. Thornton-Pett, V. Sridharan, Chem. Commun. 2002, 1372-1373; j) M. J. Remuiñán, G. Pattenden, Tetrahedron Lett. 2000, 41, 7367-7371; k) D. A. DeGoey, H.-J. Chen, W. J. Flosi, D. J. Grampovnik, C. M. Yeung, L. L. Klein, D. J. Kempf, J. Org. Chem. 2002, 67, 5445-5453; l) Y. Koriyama, A. Nozawa, R. Hayakawa, M. Shimizu, Tetrahedron 2002, 58, 9621-9628; m) D. D. Staas, K. L. Savage, C. F. Homnick, N. N. Tsou, R. G. Ball, J. Org. Chem. 2002, 67, 8276-8279; n) Z. Han, D. Krishnamurthy, D. Pflum, P. Grover, S. A. Wald, C. H. Senanayake, Org. Lett. 2002, 4, 4025-4028.
62. For a review on applications of sulfinimines, see: a) F. A. Davis, P. Zhou, B.-C. Chen, Chem. Soc. Rev. 1998, 27, 13-18; for recent leading references, see: b) F. A. Davis, K. R. Prasad, P. J. Carroll, J. Org. Chem. 2002, 67, 7802-7806; c) G. K. S. Prakash, M. Mandal, J. Am. Chem. Soc. 2002, 124, 6538-6539; d) B.-F. Li, M.-J. Zhang, X.-L. Hou, L.-X. Dai, J. Org. Chem. 2002, 67, 2902-2906; e) T. Kochi, T. P. Tang, J. A. Ellman, J. Am. Chem. Soc. 2002, 124, 6518-6519; f) V. K. Aggarwal, A. M. Martín Castro, A. Mereu, H. Adams, Tetrahedron Lett. 2002, 43, 1577-1581; g) R. Kumareswaran, A. Hassner, Tetrahedron: Asymmetry 2001, 12, 3409-3415; h) A. Asensio, P. Bravo, M. Crucianelli, A. Farina, S. Fustero, J. García Soler, S. V. Meille, W. Panzeri, F. Viani, A. Volonterio, M. Zanda, Eur. J. Org. Chem. 2001, 1449-1458; i) I. R. Cooper, R. Grigg, W. S. MacLachlan, M. Thornton-Pett, V. Sridharan, Chem. Commun. 2002, 1372-1373; j) M. J. Remuiñán, G. Pattenden, Tetrahedron Lett. 2000, 41, 7367-7371; k) D. A. DeGoey, H.-J. Chen, W. J. Flosi, D. J. Grampovnik, C. M. Yeung, L. L. Klein, D. J. Kempf, J. Org. Chem. 2002, 67, 5445-5453; l) Y. Koriyama, A. Nozawa, R. Hayakawa, M. Shimizu, Tetrahedron 2002, 58, 9621-9628; m) D. D. Staas, K. L. Savage, C. F. Homnick, N. N. Tsou, R. G. Ball, J. Org. Chem. 2002, 67, 8276-8279; n) Z. Han, D. Krishnamurthy, D. Pflum, P. Grover, S. A. Wald, C. H. Senanayake, Org. Lett. 2002, 4, 4025-4028.
63. For a review on applications of sulfinimines, see: a) F. A. Davis, P. Zhou, B.-C. Chen, Chem. Soc. Rev. 1998, 27, 13-18; for recent leading references, see: b) F. A. Davis, K. R. Prasad, P. J. Carroll, J. Org. Chem. 2002, 67, 7802-7806; c) G. K. S. Prakash, M. Mandal, J. Am. Chem. Soc. 2002, 124, 6538-6539; d) B.-F. Li, M.-J. Zhang, X.-L. Hou, L.-X. Dai, J. Org. Chem. 2002, 67, 2902-2906; e) T. Kochi, T. P. Tang, J. A. Ellman, J. Am. Chem. Soc. 2002, 124, 6518-6519; f) V. K. Aggarwal, A. M. Martín Castro, A. Mereu, H. Adams, Tetrahedron Lett. 2002, 43, 1577-1581; g) R. Kumareswaran, A. Hassner, Tetrahedron: Asymmetry 2001, 12, 3409-3415; h) A. Asensio, P. Bravo, M. Crucianelli, A. Farina, S. Fustero, J. García Soler, S. V. Meille, W. Panzeri, F. Viani, A. Volonterio, M. Zanda, Eur. J. Org. Chem. 2001, 1449-1458; i) I. R. Cooper, R. Grigg, W. S. MacLachlan, M. Thornton-Pett, V. Sridharan, Chem. Commun. 2002, 1372-1373; j) M. J. Remuiñán, G. Pattenden, Tetrahedron Lett. 2000, 41, 7367-7371; k) D. A. DeGoey, H.-J. Chen, W. J. Flosi, D. J. Grampovnik, C. M. Yeung, L. L. Klein, D. J. Kempf, J. Org. Chem. 2002, 67, 5445-5453; l) Y. Koriyama, A. Nozawa, R. Hayakawa, M. Shimizu, Tetrahedron 2002, 58, 9621-9628; m) D. D. Staas, K. L. Savage, C. F. Homnick, N. N. Tsou, R. G. Ball, J. Org. Chem. 2002, 67, 8276-8279; n) Z. Han, D. Krishnamurthy, D. Pflum, P. Grover, S. A. Wald, C. H. Senanayake, Org. Lett. 2002, 4, 4025-4028.
64. For a review on applications of sulfinimines, see: a) F. A. Davis, P. Zhou, B.-C. Chen, Chem. Soc. Rev. 1998, 27, 13-18; for recent leading references, see: b) F. A. Davis, K. R. Prasad, P. J. Carroll, J. Org. Chem. 2002, 67, 7802-7806; c) G. K. S. Prakash, M. Mandal, J. Am. Chem. Soc. 2002, 124, 6538-6539; d) B.-F. Li, M.-J. Zhang, X.-L. Hou, L.-X. Dai, J. Org. Chem. 2002, 67, 2902-2906; e) T. Kochi, T. P. Tang, J. A. Ellman, J. Am. Chem. Soc. 2002, 124, 6518-6519; f) V. K. Aggarwal, A. M. Martín Castro, A. Mereu, H. Adams, Tetrahedron Lett. 2002, 43, 1577-1581; g) R. Kumareswaran, A. Hassner, Tetrahedron: Asymmetry 2001, 12, 3409-3415; h) A. Asensio, P. Bravo, M. Crucianelli, A. Farina, S. Fustero, J. García Soler, S. V. Meille, W. Panzeri, F. Viani, A. Volonterio, M. Zanda, Eur. J. Org. Chem. 2001, 1449-1458; i) I. R. Cooper, R. Grigg, W. S. MacLachlan, M. Thornton-Pett, V. Sridharan, Chem. Commun. 2002, 1372-1373; j) M. J. Remuiñán, G. Pattenden, Tetrahedron Lett. 2000, 41, 7367-7371; k) D. A. DeGoey, H.-J. Chen, W. J. Flosi, D. J. Grampovnik, C. M. Yeung, L. L. Klein, D. J. Kempf, J. Org. Chem. 2002, 67, 5445-5453; l) Y. Koriyama, A. Nozawa, R. Hayakawa, M. Shimizu, Tetrahedron 2002, 58, 9621-9628; m) D. D. Staas, K. L. Savage, C. F. Homnick, N. N. Tsou, R. G. Ball, J. Org. Chem. 2002, 67, 8276-8279; n) Z. Han, D. Krishnamurthy, D. Pflum, P. Grover, S. A. Wald, C. H. Senanayake, Org. Lett. 2002, 4, 4025-4028.
65. For a review on applications of sulfinimines, see: a) F. A. Davis, P. Zhou, B.-C. Chen, Chem. Soc. Rev. 1998, 27, 13-18; for recent leading references, see: b) F. A. Davis, K. R. Prasad, P. J. Carroll, J. Org. Chem. 2002, 67, 7802-7806; c) G. K. S. Prakash, M. Mandal, J. Am. Chem. Soc. 2002, 124, 6538-6539; d) B.-F. Li, M.-J. Zhang, X.-L. Hou, L.-X. Dai, J. Org. Chem. 2002, 67, 2902-2906; e) T. Kochi, T. P. Tang, J. A. Ellman, J. Am. Chem. Soc. 2002, 124, 6518-6519; f) V. K. Aggarwal, A. M. Martín Castro, A. Mereu, H. Adams, Tetrahedron Lett. 2002, 43, 1577-1581; g) R. Kumareswaran, A. Hassner, Tetrahedron: Asymmetry 2001, 12, 3409-3415; h) A. Asensio, P. Bravo, M. Crucianelli, A. Farina, S. Fustero, J. García Soler, S. V. Meille, W. Panzeri, F. Viani, A. Volonterio, M. Zanda, Eur. J. Org. Chem. 2001, 1449-1458; i) I. R. Cooper, R. Grigg, W. S. MacLachlan, M. Thornton-Pett, V. Sridharan, Chem. Commun. 2002, 1372-1373; j) M. J. Remuiñán, G. Pattenden, Tetrahedron Lett. 2000, 41, 7367-7371; k) D. A. DeGoey, H.-J. Chen, W. J. Flosi, D. J. Grampovnik, C. M. Yeung, L. L. Klein, D. J. Kempf, J. Org. Chem. 2002, 67, 5445-5453; l) Y. Koriyama, A. Nozawa, R. Hayakawa, M. Shimizu, Tetrahedron 2002, 58, 9621-9628; m) D. D. Staas, K. L. Savage, C. F. Homnick, N. N. Tsou, R. G. Ball, J. Org. Chem. 2002, 67, 8276-8279; n) Z. Han, D. Krishnamurthy, D. Pflum, P. Grover, S. A. Wald, C. H. Senanayake, Org. Lett. 2002, 4, 4025-4028.
66. For a review on applications of sulfinimines, see: a) F. A. Davis, P. Zhou, B.-C. Chen, Chem. Soc. Rev. 1998, 27, 13-18; for recent leading references, see: b) F. A. Davis, K. R. Prasad, P. J. Carroll, J. Org. Chem. 2002, 67, 7802-7806; c) G. K. S. Prakash, M. Mandal, J. Am. Chem. Soc. 2002, 124, 6538-6539; d) B.-F. Li, M.-J. Zhang, X.-L. Hou, L.-X. Dai, J. Org. Chem. 2002, 67, 2902-2906; e) T. Kochi, T. P. Tang, J. A. Ellman, J. Am. Chem. Soc. 2002, 124, 6518-6519; f) V. K. Aggarwal, A. M. Martín Castro, A. Mereu, H. Adams, Tetrahedron Lett. 2002, 43, 1577-1581; g) R. Kumareswaran, A. Hassner, Tetrahedron: Asymmetry 2001, 12, 3409-3415; h) A. Asensio, P. Bravo, M. Crucianelli, A. Farina, S. Fustero, J. García Soler, S. V. Meille, W. Panzeri, F. Viani, A. Volonterio, M. Zanda, Eur. J. Org. Chem. 2001, 1449-1458; i) I. R. Cooper, R. Grigg, W. S. MacLachlan, M. Thornton-Pett, V. Sridharan, Chem. Commun. 2002, 1372-1373; j) M. J. Remuiñán, G. Pattenden, Tetrahedron Lett. 2000, 41, 7367-7371; k) D. A. DeGoey, H.-J. Chen, W. J. Flosi, D. J. Grampovnik, C. M. Yeung, L. L. Klein, D. J. Kempf, J. Org. Chem. 2002, 67, 5445-5453; l) Y. Koriyama, A. Nozawa, R. Hayakawa, M. Shimizu, Tetrahedron 2002, 58, 9621-9628; m) D. D. Staas, K. L. Savage, C. F. Homnick, N. N. Tsou, R. G. Ball, J. Org. Chem. 2002, 67, 8276-8279; n) Z. Han, D. Krishnamurthy, D. Pflum, P. Grover, S. A. Wald, C. H. Senanayake, Org. Lett. 2002, 4, 4025-4028.
67. For a review on applications of sulfinimines, see: a) F. A. Davis, P. Zhou, B.-C. Chen, Chem. Soc. Rev. 1998, 27, 13-18; for recent leading references, see: b) F. A. Davis, K. R. Prasad, P. J. Carroll, J. Org. Chem. 2002, 67, 7802-7806; c) G. K. S. Prakash, M. Mandal, J. Am. Chem. Soc. 2002, 124, 6538-6539; d) B.-F. Li, M.-J. Zhang, X.-L. Hou, L.-X. Dai, J. Org. Chem. 2002, 67, 2902-2906; e) T. Kochi, T. P. Tang, J. A. Ellman, J. Am. Chem. Soc. 2002, 124, 6518-6519; f) V. K. Aggarwal, A. M. Martín Castro, A. Mereu, H. Adams, Tetrahedron Lett. 2002, 43, 1577-1581; g) R. Kumareswaran, A. Hassner, Tetrahedron: Asymmetry 2001, 12, 3409-3415; h) A. Asensio, P. Bravo, M. Crucianelli, A. Farina, S. Fustero, J. García Soler, S. V. Meille, W. Panzeri, F. Viani, A. Volonterio, M. Zanda, Eur. J. Org. Chem. 2001, 1449-1458; i) I. R. Cooper, R. Grigg, W. S. MacLachlan, M. Thornton-Pett, V. Sridharan, Chem. Commun. 2002, 1372-1373; j) M. J. Remuiñán, G. Pattenden, Tetrahedron Lett. 2000, 41, 7367-7371; k) D. A. DeGoey, H.-J. Chen, W. J. Flosi, D. J. Grampovnik, C. M. Yeung, L. L. Klein, D. J. Kempf, J. Org. Chem. 2002, 67, 5445-5453; l) Y. Koriyama, A. Nozawa, R. Hayakawa, M. Shimizu, Tetrahedron 2002, 58, 9621-9628; m) D. D. Staas, K. L. Savage, C. F. Homnick, N. N. Tsou, R. G. Ball, J. Org. Chem. 2002, 67, 8276-8279; n) Z. Han, D. Krishnamurthy, D. Pflum, P. Grover, S. A. Wald, C. H. Senanayake, Org. Lett. 2002, 4, 4025-4028.
68. For a review on applications of sulfinimines, see: a) F. A. Davis, P. Zhou, B.-C. Chen, Chem. Soc. Rev. 1998, 27, 13-18; for recent leading references, see: b) F. A. Davis, K. R. Prasad, P. J. Carroll, J. Org. Chem. 2002, 67, 7802-7806; c) G. K. S. Prakash, M. Mandal, J. Am. Chem. Soc. 2002, 124, 6538-6539; d) B.-F. Li, M.-J. Zhang, X.-L. Hou, L.-X. Dai, J. Org. Chem. 2002, 67, 2902-2906; e) T. Kochi, T. P. Tang, J. A. Ellman, J. Am. Chem. Soc. 2002, 124, 6518-6519; f) V. K. Aggarwal, A. M. Martín Castro, A. Mereu, H. Adams, Tetrahedron Lett. 2002, 43, 1577-1581; g) R. Kumareswaran, A. Hassner, Tetrahedron: Asymmetry 2001, 12, 3409-3415; h) A. Asensio, P. Bravo, M. Crucianelli, A. Farina, S. Fustero, J. García Soler, S. V. Meille, W. Panzeri, F. Viani, A. Volonterio, M. Zanda, Eur. J. Org. Chem. 2001, 1449-1458; i) I. R. Cooper, R. Grigg, W. S. MacLachlan, M. Thornton-Pett, V. Sridharan, Chem. Commun. 2002, 1372-1373; j) M. J. Remuiñán, G. Pattenden, Tetrahedron Lett. 2000, 41, 7367-7371; k) D. A. DeGoey, H.-J. Chen, W. J. Flosi, D. J. Grampovnik, C. M. Yeung, L. L. Klein, D. J. Kempf, J. Org. Chem. 2002, 67, 5445-5453; l) Y. Koriyama, A. Nozawa, R. Hayakawa, M. Shimizu, Tetrahedron 2002, 58, 9621-9628; m) D. D. Staas, K. L. Savage, C. F. Homnick, N. N. Tsou, R. G. Ball, J. Org. Chem. 2002, 67, 8276-8279; n) Z. Han, D. Krishnamurthy, D. Pflum, P. Grover, S. A. Wald, C. H. Senanayake, Org. Lett. 2002, 4, 4025-4028.
69. For a review on applications of sulfinimines, see: a) F. A. Davis, P. Zhou, B.-C. Chen, Chem. Soc. Rev. 1998, 27, 13-18; for recent leading references, see: b) F. A. Davis, K. R. Prasad, P. J. Carroll, J. Org. Chem. 2002, 67, 7802-7806; c) G. K. S. Prakash, M. Mandal, J. Am. Chem. Soc. 2002, 124, 6538-6539; d) B.-F. Li, M.-J. Zhang, X.-L. Hou, L.-X. Dai, J. Org. Chem. 2002, 67, 2902-2906; e) T. Kochi, T. P. Tang, J. A. Ellman, J. Am. Chem. Soc. 2002, 124, 6518-6519; f) V. K. Aggarwal, A. M. Martín Castro, A. Mereu, H. Adams, Tetrahedron Lett. 2002, 43, 1577-1581; g) R. Kumareswaran, A. Hassner, Tetrahedron: Asymmetry 2001, 12, 3409-3415; h) A. Asensio, P. Bravo, M. Crucianelli, A. Farina, S. Fustero, J. García Soler, S. V. Meille, W. Panzeri, F. Viani, A. Volonterio, M. Zanda, Eur. J. Org. Chem. 2001, 1449-1458; i) I. R. Cooper, R. Grigg, W. S. MacLachlan, M. Thornton-Pett, V. Sridharan, Chem. Commun. 2002, 1372-1373; j) M. J. Remuiñán, G. Pattenden, Tetrahedron Lett. 2000, 41, 7367-7371; k) D. A. DeGoey, H.-J. Chen, W. J. Flosi, D. J. Grampovnik, C. M. Yeung, L. L. Klein, D. J. Kempf, J. Org. Chem. 2002, 67, 5445-5453; l) Y. Koriyama, A. Nozawa, R. Hayakawa, M. Shimizu, Tetrahedron 2002, 58, 9621-9628; m) D. D. Staas, K. L. Savage, C. F. Homnick, N. N. Tsou, R. G. Ball, J. Org. Chem. 2002, 67, 8276-8279; n) Z. Han, D. Krishnamurthy, D. Pflum, P. Grover, S. A. Wald, C. H. Senanayake, Org. Lett. 2002, 4, 4025-4028.
70. For a review on applications of sulfinimines, see: a) F. A. Davis, P. Zhou, B.-C. Chen, Chem. Soc. Rev. 1998, 27, 13-18; for recent leading references, see: b) F. A. Davis, K. R. Prasad, P. J. Carroll, J. Org. Chem. 2002, 67, 7802-7806; c) G. K. S. Prakash, M. Mandal, J. Am. Chem. Soc. 2002, 124, 6538-6539; d) B.-F. Li, M.-J. Zhang, X.-L. Hou, L.-X. Dai, J. Org. Chem. 2002, 67, 2902-2906; e) T. Kochi, T. P. Tang, J. A. Ellman, J. Am. Chem. Soc. 2002, 124, 6518-6519; f) V. K. Aggarwal, A. M. Martín Castro, A. Mereu, H. Adams, Tetrahedron Lett. 2002, 43, 1577-1581; g) R. Kumareswaran, A. Hassner, Tetrahedron: Asymmetry 2001, 12, 3409-3415; h) A. Asensio, P. Bravo, M. Crucianelli, A. Farina, S. Fustero, J. García Soler, S. V. Meille, W. Panzeri, F. Viani, A. Volonterio, M. Zanda, Eur. J. Org. Chem. 2001, 1449-1458; i) I. R. Cooper, R. Grigg, W. S. MacLachlan, M. Thornton-Pett, V. Sridharan, Chem. Commun. 2002, 1372-1373; j) M. J. Remuiñán, G. Pattenden, Tetrahedron Lett. 2000, 41, 7367-7371; k) D. A. DeGoey, H.-J. Chen, W. J. Flosi, D. J. Grampovnik, C. M. Yeung, L. L. Klein, D. J. Kempf, J. Org. Chem. 2002, 67, 5445-5453; l) Y. Koriyama, A. Nozawa, R. Hayakawa, M. Shimizu, Tetrahedron 2002, 58, 9621-9628; m) D. D. Staas, K. L. Savage, C. F. Homnick, N. N. Tsou, R. G. Ball, J. Org. Chem. 2002, 67, 8276-8279; n) Z. Han, D. Krishnamurthy, D. Pflum, P. Grover, S. A. Wald, C. H. Senanayake, Org. Lett. 2002, 4, 4025-4028.
71. For a review on applications of sulfinimines, see: a) F. A. Davis, P. Zhou, B.-C. Chen, Chem. Soc. Rev. 1998, 27, 13-18; for recent leading references, see: b) F. A. Davis, K. R. Prasad, P. J. Carroll, J. Org. Chem. 2002, 67, 7802-7806; c) G. K. S. Prakash, M. Mandal, J. Am. Chem. Soc. 2002, 124, 6538-6539; d) B.-F. Li, M.-J. Zhang, X.-L. Hou, L.-X. Dai, J. Org. Chem. 2002, 67, 2902-2906; e) T. Kochi, T. P. Tang, J. A. Ellman, J. Am. Chem. Soc. 2002, 124, 6518-6519; f) V. K. Aggarwal, A. M. Martín Castro, A. Mereu, H. Adams, Tetrahedron Lett. 2002, 43, 1577-1581; g) R. Kumareswaran, A. Hassner, Tetrahedron: Asymmetry 2001, 12, 3409-3415; h) A. Asensio, P. Bravo, M. Crucianelli, A. Farina, S. Fustero, J. García Soler, S. V. Meille, W. Panzeri, F. Viani, A. Volonterio, M. Zanda, Eur. J. Org. Chem. 2001, 1449-1458; i) I. R. Cooper, R. Grigg, W. S. MacLachlan, M. Thornton-Pett, V. Sridharan, Chem. Commun. 2002, 1372-1373; j) M. J. Remuiñán, G. Pattenden, Tetrahedron Lett. 2000, 41, 7367-7371; k) D. A. DeGoey, H.-J. Chen, W. J. Flosi, D. J. Grampovnik, C. M. Yeung, L. L. Klein, D. J. Kempf, J. Org. Chem. 2002, 67, 5445-5453; l) Y. Koriyama, A. Nozawa, R. Hayakawa, M. Shimizu, Tetrahedron 2002, 58, 9621-9628; m) D. D. Staas, K. L. Savage, C. F. Homnick, N. N. Tsou, R. G. Ball, J. Org. Chem. 2002, 67, 8276-8279; n) Z. Han, D. Krishnamurthy, D. Pflum, P. Grover, S. A. Wald, C. H. Senanayake, Org. Lett. 2002, 4, 4025-4028.
72. For a review on applications of sulfinimines, see: a) F. A. Davis, P. Zhou, B.-C. Chen, Chem. Soc. Rev. 1998, 27, 13-18; for recent leading references, see: b) F. A. Davis, K. R. Prasad, P. J. Carroll, J. Org. Chem. 2002, 67, 7802-7806; c) G. K. S. Prakash, M. Mandal, J. Am. Chem. Soc. 2002, 124, 6538-6539; d) B.-F. Li, M.-J. Zhang, X.-L. Hou, L.-X. Dai, J. Org. Chem. 2002, 67, 2902-2906; e) T. Kochi, T. P. Tang, J. A. Ellman, J. Am. Chem. Soc. 2002, 124, 6518-6519; f) V. K. Aggarwal, A. M. Martín Castro, A. Mereu, H. Adams, Tetrahedron Lett. 2002, 43, 1577-1581; g) R. Kumareswaran, A. Hassner, Tetrahedron: Asymmetry 2001, 12, 3409-3415; h) A. Asensio, P. Bravo, M. Crucianelli, A. Farina, S. Fustero, J. García Soler, S. V. Meille, W. Panzeri, F. Viani, A. Volonterio, M. Zanda, Eur. J. Org. Chem. 2001, 1449-1458; i) I. R. Cooper, R. Grigg, W. S. MacLachlan, M. Thornton-Pett, V. Sridharan, Chem. Commun. 2002, 1372-1373; j) M. J. Remuiñán, G. Pattenden, Tetrahedron Lett. 2000, 41, 7367-7371; k) D. A. DeGoey, H.-J. Chen, W. J. Flosi, D. J. Grampovnik, C. M. Yeung, L. L. Klein, D. J. Kempf, J. Org. Chem. 2002, 67, 5445-5453; l) Y. Koriyama, A. Nozawa, R. Hayakawa, M. Shimizu, Tetrahedron 2002, 58, 9621-9628; m) D. D. Staas, K. L. Savage, C. F. Homnick, N. N. Tsou, R. G. Ball, J. Org. Chem. 2002, 67, 8276-8279; n) Z. Han, D. Krishnamurthy, D. Pflum, P. Grover, S. A. Wald, C. H. Senanayake, Org. Lett. 2002, 4, 4025-4028.
73. For a review on applications of sulfinimines, see: a) F. A. Davis, P. Zhou, B.-C. Chen, Chem. Soc. Rev. 1998, 27, 13-18; for recent leading references, see: b) F. A. Davis, K. R. Prasad, P. J. Carroll, J. Org. Chem. 2002, 67, 7802-7806; c) G. K. S. Prakash, M. Mandal, J. Am. Chem. Soc. 2002, 124, 6538-6539; d) B.-F. Li, M.-J. Zhang, X.-L. Hou, L.-X. Dai, J. Org. Chem. 2002, 67, 2902-2906; e) T. Kochi, T. P. Tang, J. A. Ellman, J. Am. Chem. Soc. 2002, 124, 6518-6519; f) V. K. Aggarwal, A. M. Martín Castro, A. Mereu, H. Adams, Tetrahedron Lett. 2002, 43, 1577-1581; g) R. Kumareswaran, A. Hassner, Tetrahedron: Asymmetry 2001, 12, 3409-3415; h) A. Asensio, P. Bravo, M. Crucianelli, A. Farina, S. Fustero, J. García Soler, S. V. Meille, W. Panzeri, F. Viani, A. Volonterio, M. Zanda, Eur. J. Org. Chem. 2001, 1449-1458; i) I. R. Cooper, R. Grigg, W. S. MacLachlan, M. Thornton-Pett, V. Sridharan, Chem. Commun. 2002, 1372-1373; j) M. J. Remuiñán, G. Pattenden, Tetrahedron Lett. 2000, 41, 7367-7371; k) D. A. DeGoey, H.-J. Chen, W. J. Flosi, D. J. Grampovnik, C. M. Yeung, L. L. Klein, D. J. Kempf, J. Org. Chem. 2002, 67, 5445-5453; l) Y. Koriyama, A. Nozawa, R. Hayakawa, M. Shimizu, Tetrahedron 2002, 58, 9621-9628; m) D. D. Staas, K. L. Savage, C. F. Homnick, N. N. Tsou, R. G. Ball, J. Org. Chem. 2002, 67, 8276-8279; n) Z. Han, D. Krishnamurthy, D. Pflum, P. Grover, S. A. Wald, C. H. Senanayake, Org. Lett. 2002, 4, 4025-4028.
74. For a review on applications of sulfinimines, see: a) F. A. Davis, P. Zhou, B.-C. Chen, Chem. Soc. Rev. 1998, 27, 13-18; for recent leading references, see: b) F. A. Davis, K. R. Prasad, P. J. Carroll, J. Org. Chem. 2002, 67, 7802-7806; c) G. K. S. Prakash, M. Mandal, J. Am. Chem. Soc. 2002, 124, 6538-6539; d) B.-F. Li, M.-J. Zhang, X.-L. Hou, L.-X. Dai, J. Org. Chem. 2002, 67, 2902-2906; e) T. Kochi, T. P. Tang, J. A. Ellman, J. Am. Chem. Soc. 2002, 124, 6518-6519; f) V. K. Aggarwal, A. M. Martín Castro, A. Mereu, H. Adams, Tetrahedron Lett. 2002, 43, 1577-1581; g) R. Kumareswaran, A. Hassner, Tetrahedron: Asymmetry 2001, 12, 3409-3415; h) A. Asensio, P. Bravo, M. Crucianelli, A. Farina, S. Fustero, J. García Soler, S. V. Meille, W. Panzeri, F. Viani, A. Volonterio, M. Zanda, Eur. J. Org. Chem. 2001, 1449-1458; i) I. R. Cooper, R. Grigg, W. S. MacLachlan, M. Thornton-Pett, V. Sridharan, Chem. Commun. 2002, 1372-1373; j) M. J. Remuiñán, G. Pattenden, Tetrahedron Lett. 2000, 41, 7367-7371; k) D. A. DeGoey, H.-J. Chen, W. J. Flosi, D. J. Grampovnik, C. M. Yeung, L. L. Klein, D. J. Kempf, J. Org. Chem. 2002, 67, 5445-5453; l) Y. Koriyama, A. Nozawa, R. Hayakawa, M. Shimizu, Tetrahedron 2002, 58, 9621-9628; m) D. D. Staas, K. L. Savage, C. F. Homnick, N. N. Tsou, R. G. Ball, J. Org. Chem. 2002, 67, 8276-8279; n) Z. Han, D. Krishnamurthy, D. Pflum, P. Grover, S. A. Wald, C. H. Senanayake, Org. Lett. 2002, 4, 4025-4028.
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81. We have found that to ensure the reproducibility of this process the condition of the nBuLi used is critical with old bottles of reagents leading to inferior results, presumably due to the presence of important amounts of lithium salts. Furthermore, the use of an excess of nBuLi should be avoided, since the analog n-butyl ester 3a′ can be obtained as the major product instead of 3 a. Although at this point we do not have a clear explanation for this observation we cannot rule out adventitious air entering the reaction vessel upon long reaction times and forming lithium butoxide. However no change was observed in the yield and selectivity of the cycloaddition.
82. CCDC 188 087, -188 088, REBHAH, CEZSUV contains the supplementary crystallographic data for this paper and can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: (+44) 1223-336-033; or deposit@ccdc.cam.uk).
83. a) P. V. Bharatam, P. Uppal, A. Kaur, D. Kaur, J. Chem. Soc. Perkin Trans. 2 2000, 43-50;
84. b) F. A. Davis, B. Chao, T. Fang, J. M. Szewczyk, Org. Lett. 2000, 2, 1041-1043;
85. c) F. A. Davis, B. Chao, Org. Lett. 2000, 2, 2623-2625;
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89. We have attributed these failed experiments to a lack of stability of the final imidazolidines under strongly basic conditions, see: P. W. Groundwater, T. Sharif, A. Arany, D. E. Hibbs, M. B. Hursthouse, I. Garnett, M. Nyerges, J. Chem. Soc. Perkin Trans. 1 1998, 2837-2846.
90. For an example of the use of Lewis acids in dipolar cycloadditions involving azomethine ylides, see: M. Nyerges, M. Rudas, G. Tóth, B. Herényi, I. Kádas, I. Bitter, L. Töke. Tetrahedron 1995, 51, 13 321-13 330.
91. 2 is crucial for complete consumption of starting materials.
92. 3 upon raising the temperature from -78°C to -20°C and persisted after aqueous workup.
93. 4 provided a definitive structural proof for these side products along with an increase of the global yield of 7 and 8.
94. Decomposition of the starting materials upon prolonged reaction times has been tentatively proposed. For cinnamaldehyde-derived sulfinimine we cannot rule out a competition between C=N and C=C bonds as electrophiles.
95. To establish that 9a and 11a were facial isomers an equimolecular mixture of both was oxidized at sulfur with mCPBA to produce racemic N-sulfonylimidazolidine 12 a.
96. a) M. Mikolajczyk, J. Drabowicz, B. Bujnicki, J. Chem. Soc. Chem. Commun. 1976, 568-569;
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99. 2.
100. 3 solution.
101. 4/LiI in a related context, see: M. Sudharshan, P. G. Hultin, Synlett 1997, 171-172.
102. 4) to produce diastereomeric mixtures of 17g/17 g′, 15 c/c′, 15 d/d′ that were separated easily and this allowed partial characterization of the minor compounds. See experimental procedures for details.
103. Titration of nBuLi: S. C. Watson, J. E. Easthman, J. Organomet. Chem. 1967, 9, 165-168.
104. a) F. A. Davis, Y. Zhang, Y. Andemichael, T. Fang, D. L. Fanelli, H. Zhang, J. Org. Chem. 1999, 64, 1403-1406;
105. b) F. A. Davis, G. Venkat Reddy, Ch.-H. Liang, Tetrahedron Lett. 1997, 38, 5139-5142;
106. c) F. A. Davis, R. E. Reddy, J. M. Szewczyk, G. Venkat Reddy, P. S. Portonovo, T. Fang, D. L. Fanelli, R. T. Reddy, P. Zhou, P. J. Carroll, J. Org. Chem. 1997, 62, 2555-2563;
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108. L. C. Vishwakarma, O. D. Stringer, F. A. Davis, Org. Synth. Coll. Vol. VIII 1993, 546-550.
109. a) O. Tsuge, S. Kanemasa, M. Yoshioka, J. Org. Chem. 1998, 53, 1389-1391;
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