Synthesis of iridium complexes with novel planar chiral chelating imidazolylidene ligands

Tetrahedron Asymmetry

Volumn 14, Issue 12, 2003, Pages 1733-1746

  Bolm, Carsten ^a   Focken, Thilo ^a   Raabe, Gerhard ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

(ETA 4 1,5 CYCLOOCTADIENE)[1 [4 (4,4 DIMETHYL 4,5 DIHYDROOXAZOLYL)[2.2]PARACYCLOPHAN 12 YLMETHYL] 3 (2,4,6 TRIMETHYLPHENYL)IMIDAZOLIN 2 YLIDENE]IRIDIUM TETRAKIS[3,5 BIS(TRIFLUOROMETHYL)PHENYL]BORATE; (ETA 4 1,5 CYCLOOCTADIENE)[1 [4 (4,4 DIMETHYL 4,5 DIHYDROOXAZOLYL)[2.2]PARACYCLOPHAN 12 YLMETHYL] 3 METHYLIMIDAZOLIN 2 YLIDENE]IRIDIUM TETRAKIS[3,5 BIS(TRIFLUOROMETHYL)PHENYL]BORATE; (ETA 4 1,5 CYCLOOCTADIENE)[1 [4 (4,4 TERT BUTYL 4,5 DIHYDROOXAZOLYL)[2.2]PARACYCLOPHAN 12 YLMETHYL] 3 METHYLIMIDAZOLIN 2 YLIDENE]IRIDIUM TETRAKIS[3,5 BIS(TRIFLUOROMETHYL)PHENYL]BORATE; 1 [4 (4,4 DIMETHYL 4,5 DIHYDROOXAZOLYL)[2.2]PARACYCLOPHAN 12 YLMETHYL] 3 METHYLIMIDAZOLIUM BROMIDE; 4,12 DIBROMO[2.2]PARACYCLOPHANE; BORIC ACID; IMIDAZOLE DERIVATIVE; IRIDIUM COMPLEX; PARACYCLOPHANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHELATION; CHEMICAL REACTION; CHIRALITY; ENANTIOSELECTIVITY; HYDROGENATION; PRIORITY JOURNAL; PROTON TRANSPORT; SOLID STATE; STRUCTURE ANALYSIS; SYNTHESIS; X RAY ANALYSIS;

EID: 0037867656     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(03)00353-7     Document Type: Article

References (82)

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6. For reviews about NHCs and NHC-metal complexes, see: (a) Cardin, D. J.; Cetinkaya, B.; Lappert, M. F. Chem. Rev. 1972, 72, 545; (b) Herrmann, W. A.; Köcher, C. Angew. Chem. 1997, 109, 2256; Angew. Chem., Int. Ed. Engl. 1997, 36, 2163; (c) Bourissou, D.; Guerret, O.; Gabbaï, F. P.; Bertrand, G. Chem. Rev. 2000, 100, 39; (d) Herrmann, W. A. Angew. Chem. 2002, 114, 1342; Angew. Chem., Ind. Ed. 2002, 41, 1290.
7. For reviews about NHCs and NHC-metal complexes, see: (a) Cardin, D. J.; Cetinkaya, B.; Lappert, M. F. Chem. Rev. 1972, 72, 545; (b) Herrmann, W. A.; Köcher, C. Angew. Chem. 1997, 109, 2256; Angew. Chem., Int. Ed. Engl. 1997, 36, 2163; (c) Bourissou, D.; Guerret, O.; Gabbaï, F. P.; Bertrand, G. Chem. Rev. 2000, 100, 39; (d) Herrmann, W. A. Angew. Chem. 2002, 114, 1342; Angew. Chem., Ind. Ed. 2002, 41, 1290.
8. For reviews about NHCs and NHC-metal complexes, see: (a) Cardin, D. J.; Cetinkaya, B.; Lappert, M. F. Chem. Rev. 1972, 72, 545; (b) Herrmann, W. A.; Köcher, C. Angew. Chem. 1997, 109, 2256; Angew. Chem., Int. Ed. Engl. 1997, 36, 2163; (c) Bourissou, D.; Guerret, O.; Gabbaï, F. P.; Bertrand, G. Chem. Rev. 2000, 100, 39; (d) Herrmann, W. A. Angew. Chem. 2002, 114, 1342; Angew. Chem., Ind. Ed. 2002, 41, 1290.
9. For reviews about NHCs and NHC-metal complexes, see: (a) Cardin, D. J.; Cetinkaya, B.; Lappert, M. F. Chem. Rev. 1972, 72, 545; (b) Herrmann, W. A.; Köcher, C. Angew. Chem. 1997, 109, 2256; Angew. Chem., Int. Ed. Engl. 1997, 36, 2163; (c) Bourissou, D.; Guerret, O.; Gabbaï, F. P.; Bertrand, G. Chem. Rev. 2000, 100, 39; (d) Herrmann, W. A. Angew. Chem. 2002, 114, 1342; Angew. Chem., Ind. Ed. 2002, 41, 1290.
10. For reviews about NHCs and NHC-metal complexes, see: (a) Cardin, D. J.; Cetinkaya, B.; Lappert, M. F. Chem. Rev. 1972, 72, 545; (b) Herrmann, W. A.; Köcher, C. Angew. Chem. 1997, 109, 2256; Angew. Chem., Int. Ed. Engl. 1997, 36, 2163; (c) Bourissou, D.; Guerret, O.; Gabbaï, F. P.; Bertrand, G. Chem. Rev. 2000, 100, 39; (d) Herrmann, W. A. Angew. Chem. 2002, 114, 1342; Angew. Chem., Ind. Ed. 2002, 41, 1290.
11. For reviews about NHCs and NHC-metal complexes, see: (a) Cardin, D. J.; Cetinkaya, B.; Lappert, M. F. Chem. Rev. 1972, 72, 545; (b) Herrmann, W. A.; Köcher, C. Angew. Chem. 1997, 109, 2256; Angew. Chem., Int. Ed. Engl. 1997, 36, 2163; (c) Bourissou, D.; Guerret, O.; Gabbaï, F. P.; Bertrand, G. Chem. Rev. 2000, 100, 39; (d) Herrmann, W. A. Angew. Chem. 2002, 114, 1342; Angew. Chem., Ind. Ed. 2002, 41, 1290.
12. For examples of di-N-heterocyclic carbenes and their metal complexes, see: (a) Douthwaite, R. E.; Haüssinger, D.; Green, M. L. H.; Silcock, P. J.; Gomes, P. T.; Martins, A. M.; Danopoulos, A. A. Organometallics 1999, 18, 4584; (b) Douthwaite, R. E.; Green, M. L. H.; Silcock, P. J.; Gomes, P. T. Organometallics 2001, 20, 2611; (c) Douthwaite, R. E.; Green, M. L. H.; Silcock, P. J.; Gomes, P. T. J. Chem. Soc., Dalton Trans. 2002, 1386.
13. For examples of di-N-heterocyclic carbenes and their metal complexes, see: (a) Douthwaite, R. E.; Haüssinger, D.; Green, M. L. H.; Silcock, P. J.; Gomes, P. T.; Martins, A. M.; Danopoulos, A. A. Organometallics 1999, 18, 4584; (b) Douthwaite, R. E.; Green, M. L. H.; Silcock, P. J.; Gomes, P. T. Organometallics 2001, 20, 2611; (c) Douthwaite, R. E.; Green, M. L. H.; Silcock, P. J.; Gomes, P. T. J. Chem. Soc., Dalton Trans. 2002, 1386.
14. For examples of di-N-heterocyclic carbenes and their metal complexes, see: (a) Douthwaite, R. E.; Haüssinger, D.; Green, M. L. H.; Silcock, P. J.; Gomes, P. T.; Martins, A. M.; Danopoulos, A. A. Organometallics 1999, 18, 4584; (b) Douthwaite, R. E.; Green, M. L. H.; Silcock, P. J.; Gomes, P. T. Organometallics 2001, 20, 2611; (c) Douthwaite, R. E.; Green, M. L. H.; Silcock, P. J.; Gomes, P. T. J. Chem. Soc., Dalton Trans. 2002, 1386.
15. Selected references on the use of NHCs in olefin metathesis: (a) Weskamp, T.; Schattenmann, W. C.; Spiegler, M.; Herrmann, W. A. Angew. Chem. 1998, 110, 2631; Angew. Chem., Int. Ed. 1998, 37, 2490; (b) Weskamp, T.; Kohl, F. J.; Herrmann, W. A. J. Organomet. Chem. 1999, 582, 362; (c) Scholl, M.; Trnka, T. M.; Morgan, J. P.; Grubbs, R. H. Tetrahedron Lett. 1999, 40, 2247; (d) Scholl, M.; Ding, S., Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953; (e) Huang, J.; Schanz, H. Z.; Stevens, E. D.; Nolan, S. P. Organometallics 1999, 18, 5375; (f) Fürstner, A.; Ackermann, L.; Gabor, B.; Goddard, R.; Lehmann, C. W.; Mynott, R.; Stelzer, F.; Thiel, O. R. Chem. Eur. J. 2001, 7, 3236; (g) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18; (h) Sanford, M. S.; Love, J. A.; Grubbs, R. H. J. Am. Chem. Soc. 2001, 123, 6543; (i) Wakamatsu, H.; Blechert, S. Angew. Chem. 2002, 114, 2509; Angew. Chem., Int. Ed. 2002, 41, 2403; (j) Connon, S. J.; Dunne, A. M. Blechert, S. Angew. Chem. 2002, 114, 3989; Angew. Chem., Int. Ed. 2002, 41, 3835; (k) Choi, T.-L.; Rutenberg, M.; Grubbs, R. H. Angew. Chem. 2002, 114, 3995; Angew. Chem., Int. Ed. 2002, 41, 3839; (l) See also Ref. 3d.
16. Selected references on the use of NHCs in olefin metathesis: (a) Weskamp, T.; Schattenmann, W. C.; Spiegler, M.; Herrmann, W. A. Angew. Chem. 1998, 110, 2631; Angew. Chem., Int. Ed. 1998, 37, 2490; (b) Weskamp, T.; Kohl, F. J.; Herrmann, W. A. J. Organomet. Chem. 1999, 582, 362; (c) Scholl, M.; Trnka, T. M.; Morgan, J. P.; Grubbs, R. H. Tetrahedron Lett. 1999, 40, 2247; (d) Scholl, M.; Ding, S., Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953; (e) Huang, J.; Schanz, H. Z.; Stevens, E. D.; Nolan, S. P. Organometallics 1999, 18, 5375; (f) Fürstner, A.; Ackermann, L.; Gabor, B.; Goddard, R.; Lehmann, C. W.; Mynott, R.; Stelzer, F.; Thiel, O. R. Chem. Eur. J. 2001, 7, 3236; (g) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18; (h) Sanford, M. S.; Love, J. A.; Grubbs, R. H. J. Am. Chem. Soc. 2001, 123, 6543; (i) Wakamatsu, H.; Blechert, S. Angew. Chem. 2002, 114, 2509; Angew. Chem., Int. Ed. 2002, 41, 2403; (j) Connon, S. J.; Dunne, A. M. Blechert, S. Angew. Chem. 2002, 114, 3989; Angew. Chem., Int. Ed. 2002, 41, 3835; (k) Choi, T.-L.; Rutenberg, M.; Grubbs, R. H. Angew. Chem. 2002, 114, 3995; Angew. Chem., Int. Ed. 2002, 41, 3839; (l) See also Ref. 3d.
17. Selected references on the use of NHCs in olefin metathesis: (a) Weskamp, T.; Schattenmann, W. C.; Spiegler, M.; Herrmann, W. A. Angew. Chem. 1998, 110, 2631; Angew. Chem., Int. Ed. 1998, 37, 2490; (b) Weskamp, T.; Kohl, F. J.; Herrmann, W. A. J. Organomet. Chem. 1999, 582, 362; (c) Scholl, M.; Trnka, T. M.; Morgan, J. P.; Grubbs, R. H. Tetrahedron Lett. 1999, 40, 2247; (d) Scholl, M.; Ding, S., Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953; (e) Huang, J.; Schanz, H. Z.; Stevens, E. D.; Nolan, S. P. Organometallics 1999, 18, 5375; (f) Fürstner, A.; Ackermann, L.; Gabor, B.; Goddard, R.; Lehmann, C. W.; Mynott, R.; Stelzer, F.; Thiel, O. R. Chem. Eur. J. 2001, 7, 3236; (g) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18; (h) Sanford, M. S.; Love, J. A.; Grubbs, R. H. J. Am. Chem. Soc. 2001, 123, 6543; (i) Wakamatsu, H.; Blechert, S. Angew. Chem. 2002, 114, 2509; Angew. Chem., Int. Ed. 2002, 41, 2403; (j) Connon, S. J.; Dunne, A. M. Blechert, S. Angew. Chem. 2002, 114, 3989; Angew. Chem., Int. Ed. 2002, 41, 3835; (k) Choi, T.-L.; Rutenberg, M.; Grubbs, R. H. Angew. Chem. 2002, 114, 3995; Angew. Chem., Int. Ed. 2002, 41, 3839; (l) See also Ref. 3d.
18. Selected references on the use of NHCs in olefin metathesis: (a) Weskamp, T.; Schattenmann, W. C.; Spiegler, M.; Herrmann, W. A. Angew. Chem. 1998, 110, 2631; Angew. Chem., Int. Ed. 1998, 37, 2490; (b) Weskamp, T.; Kohl, F. J.; Herrmann, W. A. J. Organomet. Chem. 1999, 582, 362; (c) Scholl, M.; Trnka, T. M.; Morgan, J. P.; Grubbs, R. H. Tetrahedron Lett. 1999, 40, 2247; (d) Scholl, M.; Ding, S., Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953; (e) Huang, J.; Schanz, H. Z.; Stevens, E. D.; Nolan, S. P. Organometallics 1999, 18, 5375; (f) Fürstner, A.; Ackermann, L.; Gabor, B.; Goddard, R.; Lehmann, C. W.; Mynott, R.; Stelzer, F.; Thiel, O. R. Chem. Eur. J. 2001, 7, 3236; (g) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18; (h) Sanford, M. S.; Love, J. A.; Grubbs, R. H. J. Am. Chem. Soc. 2001, 123, 6543; (i) Wakamatsu, H.; Blechert, S. Angew. Chem. 2002, 114, 2509; Angew. Chem., Int. Ed. 2002, 41, 2403; (j) Connon, S. J.; Dunne, A. M. Blechert, S. Angew. Chem. 2002, 114, 3989; Angew. Chem., Int. Ed. 2002, 41, 3835; (k) Choi, T.-L.; Rutenberg, M.; Grubbs, R. H. Angew. Chem. 2002, 114, 3995; Angew. Chem., Int. Ed. 2002, 41, 3839; (l) See also Ref. 3d.
19. Selected references on the use of NHCs in olefin metathesis: (a) Weskamp, T.; Schattenmann, W. C.; Spiegler, M.; Herrmann, W. A. Angew. Chem. 1998, 110, 2631; Angew. Chem., Int. Ed. 1998, 37, 2490; (b) Weskamp, T.; Kohl, F. J.; Herrmann, W. A. J. Organomet. Chem. 1999, 582, 362; (c) Scholl, M.; Trnka, T. M.; Morgan, J. P.; Grubbs, R. H. Tetrahedron Lett. 1999, 40, 2247; (d) Scholl, M.; Ding, S., Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953; (e) Huang, J.; Schanz, H. Z.; Stevens, E. D.; Nolan, S. P. Organometallics 1999, 18, 5375; (f) Fürstner, A.; Ackermann, L.; Gabor, B.; Goddard, R.; Lehmann, C. W.; Mynott, R.; Stelzer, F.; Thiel, O. R. Chem. Eur. J. 2001, 7, 3236; (g) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18; (h) Sanford, M. S.; Love, J. A.; Grubbs, R. H. J. Am. Chem. Soc. 2001, 123, 6543; (i) Wakamatsu, H.; Blechert, S. Angew. Chem. 2002, 114, 2509; Angew. Chem., Int. Ed. 2002, 41, 2403; (j) Connon, S. J.; Dunne, A. M. Blechert, S. Angew. Chem. 2002, 114, 3989; Angew. Chem., Int. Ed. 2002, 41, 3835; (k) Choi, T.-L.; Rutenberg, M.; Grubbs, R. H. Angew. Chem. 2002, 114, 3995; Angew. Chem., Int. Ed. 2002, 41, 3839; (l) See also Ref. 3d.
20. Selected references on the use of NHCs in olefin metathesis: (a) Weskamp, T.; Schattenmann, W. C.; Spiegler, M.; Herrmann, W. A. Angew. Chem. 1998, 110, 2631; Angew. Chem., Int. Ed. 1998, 37, 2490; (b) Weskamp, T.; Kohl, F. J.; Herrmann, W. A. J. Organomet. Chem. 1999, 582, 362; (c) Scholl, M.; Trnka, T. M.; Morgan, J. P.; Grubbs, R. H. Tetrahedron Lett. 1999, 40, 2247; (d) Scholl, M.; Ding, S., Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953; (e) Huang, J.; Schanz, H. Z.; Stevens, E. D.; Nolan, S. P. Organometallics 1999, 18, 5375; (f) Fürstner, A.; Ackermann, L.; Gabor, B.; Goddard, R.; Lehmann, C. W.; Mynott, R.; Stelzer, F.; Thiel, O. R. Chem. Eur. J. 2001, 7, 3236; (g) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18; (h) Sanford, M. S.; Love, J. A.; Grubbs, R. H. J. Am. Chem. Soc. 2001, 123, 6543; (i) Wakamatsu, H.; Blechert, S. Angew. Chem. 2002, 114, 2509; Angew. Chem., Int. Ed. 2002, 41, 2403; (j) Connon, S. J.; Dunne, A. M. Blechert, S. Angew. Chem. 2002, 114, 3989; Angew. Chem., Int. Ed. 2002, 41, 3835; (k) Choi, T.-L.; Rutenberg, M.; Grubbs, R. H. Angew. Chem. 2002, 114, 3995; Angew. Chem., Int. Ed. 2002, 41, 3839; (l) See also Ref. 3d.
21. Selected references on the use of NHCs in olefin metathesis: (a) Weskamp, T.; Schattenmann, W. C.; Spiegler, M.; Herrmann, W. A. Angew. Chem. 1998, 110, 2631; Angew. Chem., Int. Ed. 1998, 37, 2490; (b) Weskamp, T.; Kohl, F. J.; Herrmann, W. A. J. Organomet. Chem. 1999, 582, 362; (c) Scholl, M.; Trnka, T. M.; Morgan, J. P.; Grubbs, R. H. Tetrahedron Lett. 1999, 40, 2247; (d) Scholl, M.; Ding, S., Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953; (e) Huang, J.; Schanz, H. Z.; Stevens, E. D.; Nolan, S. P. Organometallics 1999, 18, 5375; (f) Fürstner, A.; Ackermann, L.; Gabor, B.; Goddard, R.; Lehmann, C. W.; Mynott, R.; Stelzer, F.; Thiel, O. R. Chem. Eur. J. 2001, 7, 3236; (g) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18; (h) Sanford, M. S.; Love, J. A.; Grubbs, R. H. J. Am. Chem. Soc. 2001, 123, 6543; (i) Wakamatsu, H.; Blechert, S. Angew. Chem. 2002, 114, 2509; Angew. Chem., Int. Ed. 2002, 41, 2403; (j) Connon, S. J.; Dunne, A. M. Blechert, S. Angew. Chem. 2002, 114, 3989; Angew. Chem., Int. Ed. 2002, 41, 3835; (k) Choi, T.-L.; Rutenberg, M.; Grubbs, R. H. Angew. Chem. 2002, 114, 3995; Angew. Chem., Int. Ed. 2002, 41, 3839; (l) See also Ref. 3d.
22. Selected references on the use of NHCs in olefin metathesis: (a) Weskamp, T.; Schattenmann, W. C.; Spiegler, M.; Herrmann, W. A. Angew. Chem. 1998, 110, 2631; Angew. Chem., Int. Ed. 1998, 37, 2490; (b) Weskamp, T.; Kohl, F. J.; Herrmann, W. A. J. Organomet. Chem. 1999, 582, 362; (c) Scholl, M.; Trnka, T. M.; Morgan, J. P.; Grubbs, R. H. Tetrahedron Lett. 1999, 40, 2247; (d) Scholl, M.; Ding, S., Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953; (e) Huang, J.; Schanz, H. Z.; Stevens, E. D.; Nolan, S. P. Organometallics 1999, 18, 5375; (f) Fürstner, A.; Ackermann, L.; Gabor, B.; Goddard, R.; Lehmann, C. W.; Mynott, R.; Stelzer, F.; Thiel, O. R. Chem. Eur. J. 2001, 7, 3236; (g) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18; (h) Sanford, M. S.; Love, J. A.; Grubbs, R. H. J. Am. Chem. Soc. 2001, 123, 6543; (i) Wakamatsu, H.; Blechert, S. Angew. Chem. 2002, 114, 2509; Angew. Chem., Int. Ed. 2002, 41, 2403; (j) Connon, S. J.; Dunne, A. M. Blechert, S. Angew. Chem. 2002, 114, 3989; Angew. Chem., Int. Ed. 2002, 41, 3835; (k) Choi, T.-L.; Rutenberg, M.; Grubbs, R. H. Angew. Chem. 2002, 114, 3995; Angew. Chem., Int. Ed. 2002, 41, 3839; (l) See also Ref. 3d.
23. Selected references on the use of NHCs in olefin metathesis: (a) Weskamp, T.; Schattenmann, W. C.; Spiegler, M.; Herrmann, W. A. Angew. Chem. 1998, 110, 2631; Angew. Chem., Int. Ed. 1998, 37, 2490; (b) Weskamp, T.; Kohl, F. J.; Herrmann, W. A. J. Organomet. Chem. 1999, 582, 362; (c) Scholl, M.; Trnka, T. M.; Morgan, J. P.; Grubbs, R. H. Tetrahedron Lett. 1999, 40, 2247; (d) Scholl, M.; Ding, S., Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953; (e) Huang, J.; Schanz, H. Z.; Stevens, E. D.; Nolan, S. P. Organometallics 1999, 18, 5375; (f) Fürstner, A.; Ackermann, L.; Gabor, B.; Goddard, R.; Lehmann, C. W.; Mynott, R.; Stelzer, F.; Thiel, O. R. Chem. Eur. J. 2001, 7, 3236; (g) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18; (h) Sanford, M. S.; Love, J. A.; Grubbs, R. H. J. Am. Chem. Soc. 2001, 123, 6543; (i) Wakamatsu, H.; Blechert, S. Angew. Chem. 2002, 114, 2509; Angew. Chem., Int. Ed. 2002, 41, 2403; (j) Connon, S. J.; Dunne, A. M. Blechert, S. Angew. Chem. 2002, 114, 3989; Angew. Chem., Int. Ed. 2002, 41, 3835; (k) Choi, T.-L.; Rutenberg, M.; Grubbs, R. H. Angew. Chem. 2002, 114, 3995; Angew. Chem., Int. Ed. 2002, 41, 3839; (l) See also Ref. 3d.
24. Selected references on the use of NHCs in olefin metathesis: (a) Weskamp, T.; Schattenmann, W. C.; Spiegler, M.; Herrmann, W. A. Angew. Chem. 1998, 110, 2631; Angew. Chem., Int. Ed. 1998, 37, 2490; (b) Weskamp, T.; Kohl, F. J.; Herrmann, W. A. J. Organomet. Chem. 1999, 582, 362; (c) Scholl, M.; Trnka, T. M.; Morgan, J. P.; Grubbs, R. H. Tetrahedron Lett. 1999, 40, 2247; (d) Scholl, M.; Ding, S., Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953; (e) Huang, J.; Schanz, H. Z.; Stevens, E. D.; Nolan, S. P. Organometallics 1999, 18, 5375; (f) Fürstner, A.; Ackermann, L.; Gabor, B.; Goddard, R.; Lehmann, C. W.; Mynott, R.; Stelzer, F.; Thiel, O. R. Chem. Eur. J. 2001, 7, 3236; (g) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18; (h) Sanford, M. S.; Love, J. A.; Grubbs, R. H. J. Am. Chem. Soc. 2001, 123, 6543; (i) Wakamatsu, H.; Blechert, S. Angew. Chem. 2002, 114, 2509; Angew. Chem., Int. Ed. 2002, 41, 2403; (j) Connon, S. J.; Dunne, A. M. Blechert, S. Angew. Chem. 2002, 114, 3989; Angew. Chem., Int. Ed. 2002, 41, 3835; (k) Choi, T.-L.; Rutenberg, M.; Grubbs, R. H. Angew. Chem. 2002, 114, 3995; Angew. Chem., Int. Ed. 2002, 41, 3839; (l) See also Ref. 3d.
25. Selected references on the use of NHCs in olefin metathesis: (a) Weskamp, T.; Schattenmann, W. C.; Spiegler, M.; Herrmann, W. A. Angew. Chem. 1998, 110, 2631; Angew. Chem., Int. Ed. 1998, 37, 2490; (b) Weskamp, T.; Kohl, F. J.; Herrmann, W. A. J. Organomet. Chem. 1999, 582, 362; (c) Scholl, M.; Trnka, T. M.; Morgan, J. P.; Grubbs, R. H. Tetrahedron Lett. 1999, 40, 2247; (d) Scholl, M.; Ding, S., Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953; (e) Huang, J.; Schanz, H. Z.; Stevens, E. D.; Nolan, S. P. Organometallics 1999, 18, 5375; (f) Fürstner, A.; Ackermann, L.; Gabor, B.; Goddard, R.; Lehmann, C. W.; Mynott, R.; Stelzer, F.; Thiel, O. R. Chem. Eur. J. 2001, 7, 3236; (g) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18; (h) Sanford, M. S.; Love, J. A.; Grubbs, R. H. J. Am. Chem. Soc. 2001, 123, 6543; (i) Wakamatsu, H.; Blechert, S. Angew. Chem. 2002, 114, 2509; Angew. Chem., Int. Ed. 2002, 41, 2403; (j) Connon, S. J.; Dunne, A. M. Blechert, S. Angew. Chem. 2002, 114, 3989; Angew. Chem., Int. Ed. 2002, 41, 3835; (k) Choi, T.-L.; Rutenberg, M.; Grubbs, R. H. Angew. Chem. 2002, 114, 3995; Angew. Chem., Int. Ed. 2002, 41, 3839; (l) See also Ref. 3d.
26. Selected references on the use of NHCs in olefin metathesis: (a) Weskamp, T.; Schattenmann, W. C.; Spiegler, M.; Herrmann, W. A. Angew. Chem. 1998, 110, 2631; Angew. Chem., Int. Ed. 1998, 37, 2490; (b) Weskamp, T.; Kohl, F. J.; Herrmann, W. A. J. Organomet. Chem. 1999, 582, 362; (c) Scholl, M.; Trnka, T. M.; Morgan, J. P.; Grubbs, R. H. Tetrahedron Lett. 1999, 40, 2247; (d) Scholl, M.; Ding, S., Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953; (e) Huang, J.; Schanz, H. Z.; Stevens, E. D.; Nolan, S. P. Organometallics 1999, 18, 5375; (f) Fürstner, A.; Ackermann, L.; Gabor, B.; Goddard, R.; Lehmann, C. W.; Mynott, R.; Stelzer, F.; Thiel, O. R. Chem. Eur. J. 2001, 7, 3236; (g) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18; (h) Sanford, M. S.; Love, J. A.; Grubbs, R. H. J. Am. Chem. Soc. 2001, 123, 6543; (i) Wakamatsu, H.; Blechert, S. Angew. Chem. 2002, 114, 2509; Angew. Chem., Int. Ed. 2002, 41, 2403; (j) Connon, S. J.; Dunne, A. M. Blechert, S. Angew. Chem. 2002, 114, 3989; Angew. Chem., Int. Ed. 2002, 41, 3835; (k) Choi, T.-L.; Rutenberg, M.; Grubbs, R. H. Angew. Chem. 2002, 114, 3995; Angew. Chem., Int. Ed. 2002, 41, 3839; (l) See also Ref. 3d.
27. Selected references on the use of NHCs in olefin metathesis: (a) Weskamp, T.; Schattenmann, W. C.; Spiegler, M.; Herrmann, W. A. Angew. Chem. 1998, 110, 2631; Angew. Chem., Int. Ed. 1998, 37, 2490; (b) Weskamp, T.; Kohl, F. J.; Herrmann, W. A. J. Organomet. Chem. 1999, 582, 362; (c) Scholl, M.; Trnka, T. M.; Morgan, J. P.; Grubbs, R. H. Tetrahedron Lett. 1999, 40, 2247; (d) Scholl, M.; Ding, S., Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953; (e) Huang, J.; Schanz, H. Z.; Stevens, E. D.; Nolan, S. P. Organometallics 1999, 18, 5375; (f) Fürstner, A.; Ackermann, L.; Gabor, B.; Goddard, R.; Lehmann, C. W.; Mynott, R.; Stelzer, F.; Thiel, O. R. Chem. Eur. J. 2001, 7, 3236; (g) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18; (h) Sanford, M. S.; Love, J. A.; Grubbs, R. H. J. Am. Chem. Soc. 2001, 123, 6543; (i) Wakamatsu, H.; Blechert, S. Angew. Chem. 2002, 114, 2509; Angew. Chem., Int. Ed. 2002, 41, 2403; (j) Connon, S. J.; Dunne, A. M. Blechert, S. Angew. Chem. 2002, 114, 3989; Angew. Chem., Int. Ed. 2002, 41, 3835; (k) Choi, T.-L.; Rutenberg, M.; Grubbs, R. H. Angew. Chem. 2002, 114, 3995; Angew. Chem., Int. Ed. 2002, 41, 3839; (l) See also Ref. 3d.
28. Selected references on the use of NHCs in olefin metathesis: (a) Weskamp, T.; Schattenmann, W. C.; Spiegler, M.; Herrmann, W. A. Angew. Chem. 1998, 110, 2631; Angew. Chem., Int. Ed. 1998, 37, 2490; (b) Weskamp, T.; Kohl, F. J.; Herrmann, W. A. J. Organomet. Chem. 1999, 582, 362; (c) Scholl, M.; Trnka, T. M.; Morgan, J. P.; Grubbs, R. H. Tetrahedron Lett. 1999, 40, 2247; (d) Scholl, M.; Ding, S., Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953; (e) Huang, J.; Schanz, H. Z.; Stevens, E. D.; Nolan, S. P. Organometallics 1999, 18, 5375; (f) Fürstner, A.; Ackermann, L.; Gabor, B.; Goddard, R.; Lehmann, C. W.; Mynott, R.; Stelzer, F.; Thiel, O. R. Chem. Eur. J. 2001, 7, 3236; (g) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18; (h) Sanford, M. S.; Love, J. A.; Grubbs, R. H. J. Am. Chem. Soc. 2001, 123, 6543; (i) Wakamatsu, H.; Blechert, S. Angew. Chem. 2002, 114, 2509; Angew. Chem., Int. Ed. 2002, 41, 2403; (j) Connon, S. J.; Dunne, A. M. Blechert, S. Angew. Chem. 2002, 114, 3989; Angew. Chem., Int. Ed. 2002, 41, 3835; (k) Choi, T.-L.; Rutenberg, M.; Grubbs, R. H. Angew. Chem. 2002, 114, 3995; Angew. Chem., Int. Ed. 2002, 41, 3839; (l) See also Ref. 3d.
29. Selected references on the use of NHCs in olefin metathesis: (a) Weskamp, T.; Schattenmann, W. C.; Spiegler, M.; Herrmann, W. A. Angew. Chem. 1998, 110, 2631; Angew. Chem., Int. Ed. 1998, 37, 2490; (b) Weskamp, T.; Kohl, F. J.; Herrmann, W. A. J. Organomet. Chem. 1999, 582, 362; (c) Scholl, M.; Trnka, T. M.; Morgan, J. P.; Grubbs, R. H. Tetrahedron Lett. 1999, 40, 2247; (d) Scholl, M.; Ding, S., Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953; (e) Huang, J.; Schanz, H. Z.; Stevens, E. D.; Nolan, S. P. Organometallics 1999, 18, 5375; (f) Fürstner, A.; Ackermann, L.; Gabor, B.; Goddard, R.; Lehmann, C. W.; Mynott, R.; Stelzer, F.; Thiel, O. R. Chem. Eur. J. 2001, 7, 3236; (g) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18; (h) Sanford, M. S.; Love, J. A.; Grubbs, R. H. J. Am. Chem. Soc. 2001, 123, 6543; (i) Wakamatsu, H.; Blechert, S. Angew. Chem. 2002, 114, 2509; Angew. Chem., Int. Ed. 2002, 41, 2403; (j) Connon, S. J.; Dunne, A. M. Blechert, S. Angew. Chem. 2002, 114, 3989; Angew. Chem., Int. Ed. 2002, 41, 3835; (k) Choi, T.-L.; Rutenberg, M.; Grubbs, R. H. Angew. Chem. 2002, 114, 3995; Angew. Chem., Int. Ed. 2002, 41, 3839; (l) See also Ref. 3d.
30. Selected references on the use of NHCs in olefin metathesis: (a) Weskamp, T.; Schattenmann, W. C.; Spiegler, M.; Herrmann, W. A. Angew. Chem. 1998, 110, 2631; Angew. Chem., Int. Ed. 1998, 37, 2490; (b) Weskamp, T.; Kohl, F. J.; Herrmann, W. A. J. Organomet. Chem. 1999, 582, 362; (c) Scholl, M.; Trnka, T. M.; Morgan, J. P.; Grubbs, R. H. Tetrahedron Lett. 1999, 40, 2247; (d) Scholl, M.; Ding, S., Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953; (e) Huang, J.; Schanz, H. Z.; Stevens, E. D.; Nolan, S. P. Organometallics 1999, 18, 5375; (f) Fürstner, A.; Ackermann, L.; Gabor, B.; Goddard, R.; Lehmann, C. W.; Mynott, R.; Stelzer, F.; Thiel, O. R. Chem. Eur. J. 2001, 7, 3236; (g) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18; (h) Sanford, M. S.; Love, J. A.; Grubbs, R. H. J. Am. Chem. Soc. 2001, 123, 6543; (i) Wakamatsu, H.; Blechert, S. Angew. Chem. 2002, 114, 2509; Angew. Chem., Int. Ed. 2002, 41, 2403; (j) Connon, S. J.; Dunne, A. M. Blechert, S. Angew. Chem. 2002, 114, 3989; Angew. Chem., Int. Ed. 2002, 41, 3835; (k) Choi, T.-L.; Rutenberg, M.; Grubbs, R. H. Angew. Chem. 2002, 114, 3995; Angew. Chem., Int. Ed. 2002, 41, 3839; (l) See also Ref. 3d.
31. Lee H.M., Smith D.C. Jr., He Z., Stevens E.D., Yi C.S., Nolan S.P. Organometallics. 20:2001;794.
32. Lee H.M., Jiang T., Stevens E.D., Nolan S.P. Organometallics. 20:2001;1255.
33. Hillier A.C., Lee H.M., Stevens E.D., Nolan S.P. Organometallics. 20:2001;4246.
34. For a complex of type 1, where the pyridine is replaced by a phosphine, see: Vázques-Serrano L.D., Owens B.T., Buriak J.M. Chem. Commun. 2002;2518.
35. Albrecht M., Crabtree R.H., Mata J., Peris E. Chem. Commun. 2002;32.
36. Albrecht M., Miecznikowski J.R., Samuel A., Faller J.W., Crabtree R.H. Organometallics. 21:2002;3596.
37. Herrmann, W. A.; Gooßen, L. J.; Köcher, C.; Artus, G. R. J. Angew. Chem. 1996, 108, 2980; Angew. Chem., Int. Ed. Engl. 1996, 35, 2805.
38. Herrmann W.A., Gooßen L.J., Artus G.R.J., Köcher C. Organometallics. 16:1997;2472.
39. Enders D., Gielen H., Breuer K. Tetrahedron: Asymmetry. 8:1997;3571.
40. Enders D., Gielen H. J. Organomet. Chem. 617-618:2001;70.
41. Seiders T.J., Ward D.W., Grubbs R.H. Org. Lett. 3:2001;3225.
42. Van Veldhuizen J.J., Garber S.B., Kingsbury J.S., Hoveyda A.H. J. Am. Chem. Soc. 124:2002;4954.
43. Review: Hoveyda A.H., Schrock R.R. Chem. Eur. J. 7:2001;945.
44. Pytkowicz J., Roland S., Mangeney P. Tetrahedron: Asymmetry. 12:2001;2087.
45. Enders D., Breuer K. Helv. Chim. Acta. 79:1996;1217.
46. Enders D., Breuer K., Runsink J. Helv. Chim. Acta. 79:1996;1899 Enders, D.; Kallfass, U. Angew. Chem. 2002, 114, 1822; Angew. Chem., Int. Ed. 2002, 41, 1743.
47. Enders D., Breuer K., Runsink J. Helv. Chim. Acta. 79:1996;1899 Enders, D.; Kallfass, U. Angew. Chem. 2002, 114, 1822; Angew. Chem., Int. Ed. 2002, 41, 1743.
48. Enders D., Breuer K., Runsink J. Helv. Chim. Acta. 79:1996;1899 Enders, D.; Kallfass, U. Angew. Chem. 2002, 114, 1822; Angew. Chem., Int. Ed. 2002, 41, 1743.
49. Powell M.T., Hou D.-R., Perry M.C., Cui X., Burgess K. J. Am. Chem. Soc. 112:2001;8878.
50. Perry M.C., Cui X., Powell M.T., Hou D.-R., Reibenspiess J.H., Burgess K. J. Am. Chem. Soc. 125:2003;113 Recently, the application of ferrocene-based Rh and Ir NHC complexes in the hydrogenation of dimethylitaconate (44% yield, 18% ee) has been reported. Seo, H.; Park, H.-J.; Kim, B. Y.; Lee, J. H.; Son, S. U.; Chung, Y. K. Organometallics 2003, 22, 618.
51. Perry M.C., Cui X., Powell M.T., Hou D.-R., Reibenspiess J.H., Burgess K. J. Am. Chem. Soc. 125:2003;113 Recently, the application of ferrocene-based Rh and Ir NHC complexes in the hydrogenation of dimethylitaconate (44% yield, 18% ee) has been reported. Seo, H.; Park, H.-J.; Kim, B. Y.; Lee, J. H.; Son, S. U.; Chung, Y. K. Organometallics 2003, 22, 618.
52. Bolm C., Kesselgruber M., Raabe G. Organometallics. 21:2002;707.
53. 2-symmetric carbene, see: Broggini D., Togni A. Helv. Chim. Acta. 85:2002;2518.
54. For other pseudo-ortho-disubstituted [2.2]paracyclophanes having phosphorous-containing substituents, see: (a) Pye, P. J.; Rossen, K.; Reamer, R. A.; Tsou, N. N.; Volante, R. P.; Reider, P. J. J. Am. Chem. Soc. 1997, 119, 6207; (b) Pye, P. J.; Rossen, K.; Volante, R. P. Merck & Co., PCT Appl. WO 97/47632, 1997; (c) Pye, P. J.; Rossen, K.; Reamer, R. A.; Volante, R. P.; Reider, P. J. Tetrahedron Lett. 1998, 39, 4441; (d) Dyer, P. W.; Dyson, P. J.; James, S. L.; Martin, C. M.; Suman, P. Organometallics 1998, 17, 4344; (e) Burk, M. J.; Hems, W.; Herzberg, D.; Malan, C.; Zanotti-Gerosa, A. Org. Lett. 2000, 2, 4173; (f) Zanotti-Gerosa, A.; Malan, C.; Herzberg, D. Org. Lett. 2001, 3, 3687; (g) Rossen, K. Angew. Chem. 2001, 113, 4747; Angew. Chem., Int. Ed. 2001, 40, 4611.
55. For other pseudo-ortho-disubstituted [2.2]paracyclophanes having phosphorous-containing substituents, see: (a) Pye, P. J.; Rossen, K.; Reamer, R. A.; Tsou, N. N.; Volante, R. P.; Reider, P. J. J. Am. Chem. Soc. 1997, 119, 6207; (b) Pye, P. J.; Rossen, K.; Volante, R. P. Merck & Co., PCT Appl. WO 97/47632, 1997; (c) Pye, P. J.; Rossen, K.; Reamer, R. A.; Volante, R. P.; Reider, P. J. Tetrahedron Lett. 1998, 39, 4441; (d) Dyer, P. W.; Dyson, P. J.; James, S. L.; Martin, C. M.; Suman, P. Organometallics 1998, 17, 4344; (e) Burk, M. J.; Hems, W.; Herzberg, D.; Malan, C.; Zanotti-Gerosa, A. Org. Lett. 2000, 2, 4173; (f) Zanotti-Gerosa, A.; Malan, C.; Herzberg, D. Org. Lett. 2001, 3, 3687; (g) Rossen, K. Angew. Chem. 2001, 113, 4747; Angew. Chem., Int. Ed. 2001, 40, 4611.
56. For other pseudo-ortho-disubstituted [2.2]paracyclophanes having phosphorous-containing substituents, see: (a) Pye, P. J.; Rossen, K.; Reamer, R. A.; Tsou, N. N.; Volante, R. P.; Reider, P. J. J. Am. Chem. Soc. 1997, 119, 6207; (b) Pye, P. J.; Rossen, K.; Volante, R. P. Merck & Co., PCT Appl. WO 97/47632, 1997; (c) Pye, P. J.; Rossen, K.; Reamer, R. A.; Volante, R. P.; Reider, P. J. Tetrahedron Lett. 1998, 39, 4441; (d) Dyer, P. W.; Dyson, P. J.; James, S. L.; Martin, C. M.; Suman, P. Organometallics 1998, 17, 4344; (e) Burk, M. J.; Hems, W.; Herzberg, D.; Malan, C.; Zanotti-Gerosa, A. Org. Lett. 2000, 2, 4173; (f) Zanotti-Gerosa, A.; Malan, C.; Herzberg, D. Org. Lett. 2001, 3, 3687; (g) Rossen, K. Angew. Chem. 2001, 113, 4747; Angew. Chem., Int. Ed. 2001, 40, 4611.
57. For other pseudo-ortho-disubstituted [2.2]paracyclophanes having phosphorous-containing substituents, see: (a) Pye, P. J.; Rossen, K.; Reamer, R. A.; Tsou, N. N.; Volante, R. P.; Reider, P. J. J. Am. Chem. Soc. 1997, 119, 6207; (b) Pye, P. J.; Rossen, K.; Volante, R. P. Merck & Co., PCT Appl. WO 97/47632, 1997; (c) Pye, P. J.; Rossen, K.; Reamer, R. A.; Volante, R. P.; Reider, P. J. Tetrahedron Lett. 1998, 39, 4441; (d) Dyer, P. W.; Dyson, P. J.; James, S. L.; Martin, C. M.; Suman, P. Organometallics 1998, 17, 4344; (e) Burk, M. J.; Hems, W.; Herzberg, D.; Malan, C.; Zanotti-Gerosa, A. Org. Lett. 2000, 2, 4173; (f) Zanotti-Gerosa, A.; Malan, C.; Herzberg, D. Org. Lett. 2001, 3, 3687; (g) Rossen, K. Angew. Chem. 2001, 113, 4747; Angew. Chem., Int. Ed. 2001, 40, 4611.
58. For other pseudo-ortho-disubstituted [2.2]paracyclophanes having phosphorous-containing substituents, see: (a) Pye, P. J.; Rossen, K.; Reamer, R. A.; Tsou, N. N.; Volante, R. P.; Reider, P. J. J. Am. Chem. Soc. 1997, 119, 6207; (b) Pye, P. J.; Rossen, K.; Volante, R. P. Merck & Co., PCT Appl. WO 97/47632, 1997; (c) Pye, P. J.; Rossen, K.; Reamer, R. A.; Volante, R. P.; Reider, P. J. Tetrahedron Lett. 1998, 39, 4441; (d) Dyer, P. W.; Dyson, P. J.; James, S. L.; Martin, C. M.; Suman, P. Organometallics 1998, 17, 4344; (e) Burk, M. J.; Hems, W.; Herzberg, D.; Malan, C.; Zanotti-Gerosa, A. Org. Lett. 2000, 2, 4173; (f) Zanotti-Gerosa, A.; Malan, C.; Herzberg, D. Org. Lett. 2001, 3, 3687; (g) Rossen, K. Angew. Chem. 2001, 113, 4747; Angew. Chem., Int. Ed. 2001, 40, 4611.
59. For other pseudo-ortho-disubstituted [2.2]paracyclophanes having phosphorous-containing substituents, see: (a) Pye, P. J.; Rossen, K.; Reamer, R. A.; Tsou, N. N.; Volante, R. P.; Reider, P. J. J. Am. Chem. Soc. 1997, 119, 6207; (b) Pye, P. J.; Rossen, K.; Volante, R. P. Merck & Co., PCT Appl. WO 97/47632, 1997; (c) Pye, P. J.; Rossen, K.; Reamer, R. A.; Volante, R. P.; Reider, P. J. Tetrahedron Lett. 1998, 39, 4441; (d) Dyer, P. W.; Dyson, P. J.; James, S. L.; Martin, C. M.; Suman, P. Organometallics 1998, 17, 4344; (e) Burk, M. J.; Hems, W.; Herzberg, D.; Malan, C.; Zanotti-Gerosa, A. Org. Lett. 2000, 2, 4173; (f) Zanotti-Gerosa, A.; Malan, C.; Herzberg, D. Org. Lett. 2001, 3, 3687; (g) Rossen, K. Angew. Chem. 2001, 113, 4747; Angew. Chem., Int. Ed. 2001, 40, 4611.
60. For other pseudo-ortho-disubstituted [2.2]paracyclophanes having phosphorous-containing substituents, see: (a) Pye, P. J.; Rossen, K.; Reamer, R. A.; Tsou, N. N.; Volante, R. P.; Reider, P. J. J. Am. Chem. Soc. 1997, 119, 6207; (b) Pye, P. J.; Rossen, K.; Volante, R. P. Merck & Co., PCT Appl. WO 97/47632, 1997; (c) Pye, P. J.; Rossen, K.; Reamer, R. A.; Volante, R. P.; Reider, P. J. Tetrahedron Lett. 1998, 39, 4441; (d) Dyer, P. W.; Dyson, P. J.; James, S. L.; Martin, C. M.; Suman, P. Organometallics 1998, 17, 4344; (e) Burk, M. J.; Hems, W.; Herzberg, D.; Malan, C.; Zanotti-Gerosa, A. Org. Lett. 2000, 2, 4173; (f) Zanotti-Gerosa, A.; Malan, C.; Herzberg, D. Org. Lett. 2001, 3, 3687; (g) Rossen, K. Angew. Chem. 2001, 113, 4747; Angew. Chem., Int. Ed. 2001, 40, 4611.
61. For other pseudo-ortho-disubstituted [2.2]paracyclophanes having phosphorous-containing substituents, see: (a) Pye, P. J.; Rossen, K.; Reamer, R. A.; Tsou, N. N.; Volante, R. P.; Reider, P. J. J. Am. Chem. Soc. 1997, 119, 6207; (b) Pye, P. J.; Rossen, K.; Volante, R. P. Merck & Co., PCT Appl. WO 97/47632, 1997; (c) Pye, P. J.; Rossen, K.; Reamer, R. A.; Volante, R. P.; Reider, P. J. Tetrahedron Lett. 1998, 39, 4441; (d) Dyer, P. W.; Dyson, P. J.; James, S. L.; Martin, C. M.; Suman, P. Organometallics 1998, 17, 4344; (e) Burk, M. J.; Hems, W.; Herzberg, D.; Malan, C.; Zanotti-Gerosa, A. Org. Lett. 2000, 2, 4173; (f) Zanotti-Gerosa, A.; Malan, C.; Herzberg, D. Org. Lett. 2001, 3, 3687; (g) Rossen, K. Angew. Chem. 2001, 113, 4747; Angew. Chem., Int. Ed. 2001, 40, 4611.
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68. (a) For comparison of reactivities in hydrogenations, see (a): Schnider, P.; Koch, G.; Prétôt, R.; Wang, G.; Bohnen, F. M.; Krüger, C.; Pfaltz, A. Chem. Eur. J. 1997, 3, 887; (b) Kainz, S.; Brinkmann, A.; Leitner, W.; Pfaltz, A. J. Am. Chem. Soc. 1999, 121, 6421; (c) Drago, D.; Pregosin, P. S.; Pfaltz, A. Chem. Commun. 2002, 286.
69. (a) For comparison of reactivities in hydrogenations, see (a): Schnider, P.; Koch, G.; Prétôt, R.; Wang, G.; Bohnen, F. M.; Krüger, C.; Pfaltz, A. Chem. Eur. J. 1997, 3, 887; (b) Kainz, S.; Brinkmann, A.; Leitner, W.; Pfaltz, A. J. Am. Chem. Soc. 1999, 121, 6421; (c) Drago, D.; Pregosin, P. S.; Pfaltz, A. Chem. Commun. 2002, 286.
70. (a) For comparison of reactivities in hydrogenations, see (a): Schnider, P.; Koch, G.; Prétôt, R.; Wang, G.; Bohnen, F. M.; Krüger, C.; Pfaltz, A. Chem. Eur. J. 1997, 3, 887; (b) Kainz, S.; Brinkmann, A.; Leitner, W.; Pfaltz, A. J. Am. Chem. Soc. 1999, 121, 6421; (c) Drago, D.; Pregosin, P. S.; Pfaltz, A. Chem. Commun. 2002, 286.
71. For other Ir-catalyzed asymmetric hydrogenation of unfunctionalized alkenes, see: (a) Lightfoot, A.; Schnider, P.; Pfaltz, A. Angew. Chem. 1998, 110, 3047; Angew. Chem., Int. Ed. 1998, 37, 2897; (b) Blankenstein, J.; Pfaltz, A. Angew. Chem. 2001, 113, 4577; Angew. Chem., Int. Ed. 2001, 40, 4445; (c) Cozzi, P. G.; Zimmermann, N.; Hilgraf, R.; Schaffner, S.; Pfaltz, A. Adv. Synth. Catal. 2001, 343, 450; (d) Hou, D.-R.; Reibenspies, J.; Colacot, T. J.; Burgess, K. Chem. Eur. J. 2001, 7, 5391; (e) Menges, F.; Pfaltz, A. Adv. Synth. Catal. 2002, 344, 40; (f) for a review, see: Pfaltz, A.; Blankenstein, J.; Hilgraf, R.; Hörmann, E.; McIntyre, S.; Menges, F.; Schönleber, M.; Smidt, S. P.; Wüstenberg, B.; Zimmermann, N. Adv. Synth. Catal. 2003, 345, 33.
72. For other Ir-catalyzed asymmetric hydrogenation of unfunctionalized alkenes, see: (a) Lightfoot, A.; Schnider, P.; Pfaltz, A. Angew. Chem. 1998, 110, 3047; Angew. Chem., Int. Ed. 1998, 37, 2897; (b) Blankenstein, J.; Pfaltz, A. Angew. Chem. 2001, 113, 4577; Angew. Chem., Int. Ed. 2001, 40, 4445; (c) Cozzi, P. G.; Zimmermann, N.; Hilgraf, R.; Schaffner, S.; Pfaltz, A. Adv. Synth. Catal. 2001, 343, 450; (d) Hou, D.-R.; Reibenspies, J.; Colacot, T. J.; Burgess, K. Chem. Eur. J. 2001, 7, 5391; (e) Menges, F.; Pfaltz, A. Adv. Synth. Catal. 2002, 344, 40; (f) for a review, see: Pfaltz, A.; Blankenstein, J.; Hilgraf, R.; Hörmann, E.; McIntyre, S.; Menges, F.; Schönleber, M.; Smidt, S. P.; Wüstenberg, B.; Zimmermann, N. Adv. Synth. Catal. 2003, 345, 33.9
73. For other Ir-catalyzed asymmetric hydrogenation of unfunctionalized alkenes, see: (a) Lightfoot, A.; Schnider, P.; Pfaltz, A. Angew. Chem. 1998, 110, 3047; Angew. Chem., Int. Ed. 1998, 37, 2897; (b) Blankenstein, J.; Pfaltz, A. Angew. Chem. 2001, 113, 4577; Angew. Chem., Int. Ed. 2001, 40, 4445; (c) Cozzi, P. G.; Zimmermann, N.; Hilgraf, R.; Schaffner, S.; Pfaltz, A. Adv. Synth. Catal. 2001, 343, 450; (d) Hou, D.-R.; Reibenspies, J.; Colacot, T. J.; Burgess, K. Chem. Eur. J. 2001, 7, 5391; (e) Menges, F.; Pfaltz, A. Adv. Synth. Catal. 2002, 344, 40; (f) for a review, see: Pfaltz, A.; Blankenstein, J.; Hilgraf, R.; Hörmann, E.; McIntyre, S.; Menges, F.; Schönleber, M.; Smidt, S. P.; Wüstenberg, B.; Zimmermann, N. Adv. Synth. Catal. 2003, 345, 33.
74. For other Ir-catalyzed asymmetric hydrogenation of unfunctionalized alkenes, see: (a) Lightfoot, A.; Schnider, P.; Pfaltz, A. Angew. Chem. 1998, 110, 3047; Angew. Chem., Int. Ed. 1998, 37, 2897; (b) Blankenstein, J.; Pfaltz, A. Angew. Chem. 2001, 113, 4577; Angew. Chem., Int. Ed. 2001, 40, 4445; (c) Cozzi, P. G.; Zimmermann, N.; Hilgraf, R.; Schaffner, S.; Pfaltz, A. Adv. Synth. Catal. 2001, 343, 450; (d) Hou, D.-R.; Reibenspies, J.; Colacot, T. J.; Burgess, K. Chem. Eur. J. 2001, 7, 5391; (e) Menges, F.; Pfaltz, A. Adv. Synth. Catal. 2002, 344, 40; (f) for a review, see: Pfaltz, A.; Blankenstein, J.; Hilgraf, R.; Hörmann, E.; McIntyre, S.; Menges, F.; Schönleber, M.; Smidt, S. P.; Wüstenberg, B.; Zimmermann, N. Adv. Synth. Catal. 2003, 345, 33.
75. For other Ir-catalyzed asymmetric hydrogenation of unfunctionalized alkenes, see: (a) Lightfoot, A.; Schnider, P.; Pfaltz, A. Angew. Chem. 1998, 110, 3047; Angew. Chem., Int. Ed. 1998, 37, 2897; (b) Blankenstein, J.; Pfaltz, A. Angew. Chem. 2001, 113, 4577; Angew. Chem., Int. Ed. 2001, 40, 4445; (c) Cozzi, P. G.; Zimmermann, N.; Hilgraf, R.; Schaffner, S.; Pfaltz, A. Adv. Synth. Catal. 2001, 343, 450; (d) Hou, D.-R.; Reibenspies, J.; Colacot, T. J.; Burgess, K. Chem. Eur. J. 2001, 7, 5391; (e) Menges, F.; Pfaltz, A. Adv. Synth. Catal. 2002, 344, 40; (f) for a review, see: Pfaltz, A.; Blankenstein, J.; Hilgraf, R.; Hörmann, E.; McIntyre, S.; Menges, F.; Schönleber, M.; Smidt, S. P.; Wüstenberg, B.; Zimmermann, N. Adv. Synth. Catal. 2003, 345, 33.
76. For other Ir-catalyzed asymmetric hydrogenation of unfunctionalized alkenes, see: (a) Lightfoot, A.; Schnider, P.; Pfaltz, A. Angew. Chem. 1998, 110, 3047; Angew. Chem., Int. Ed. 1998, 37, 2897; (b) Blankenstein, J.; Pfaltz, A. Angew. Chem. 2001, 113, 4577; Angew. Chem., Int. Ed. 2001, 40, 4445; (c) Cozzi, P. G.; Zimmermann, N.; Hilgraf, R.; Schaffner, S.; Pfaltz, A. Adv. Synth. Catal. 2001, 343, 450; (d) Hou, D.-R.; Reibenspies, J.; Colacot, T. J.; Burgess, K. Chem. Eur. J. 2001, 7, 5391; (e) Menges, F.; Pfaltz, A. Adv. Synth. Catal. 2002, 344, 40; (f) for a review, see: Pfaltz, A.; Blankenstein, J.; Hilgraf, R.; Hörmann, E.; McIntyre, S.; Menges, F.; Schönleber, M.; Smidt, S. P.; Wüstenberg, B.; Zimmermann, N. Adv. Synth. Catal. 2003, 345, 33.
77. For other Ir-catalyzed asymmetric hydrogenation of unfunctionalized alkenes, see: (a) Lightfoot, A.; Schnider, P.; Pfaltz, A. Angew. Chem. 1998, 110, 3047; Angew. Chem., Int. Ed. 1998, 37, 2897; (b) Blankenstein, J.; Pfaltz, A. Angew. Chem. 2001, 113, 4577; Angew. Chem., Int. Ed. 2001, 40, 4445; (c) Cozzi, P. G.; Zimmermann, N.; Hilgraf, R.; Schaffner, S.; Pfaltz, A. Adv. Synth. Catal. 2001, 343, 450; (d) Hou, D.-R.; Reibenspies, J.; Colacot, T. J.; Burgess, K. Chem. Eur. J. 2001, 7, 5391; (e) Menges, F.; Pfaltz, A. Adv. Synth. Catal. 2002, 344, 40; (f) for a review, see: Pfaltz, A.; Blankenstein, J.; Hilgraf, R.; Hörmann, E.; McIntyre, S.; Menges, F.; Schönleber, M.; Smidt, S. P.; Wüstenberg, B.; Zimmermann, N. Adv. Synth. Catal. 2003, 345, 33.
78. For other Ir-catalyzed asymmetric hydrogenation of unfunctionalized alkenes, see: (a) Lightfoot, A.; Schnider, P.; Pfaltz, A. Angew. Chem. 1998, 110, 3047; Angew. Chem., Int. Ed. 1998, 37, 2897; (b) Blankenstein, J.; Pfaltz, A. Angew. Chem. 2001, 113, 4577; Angew. Chem., Int. Ed. 2001, 40, 4445; (c) Cozzi, P. G.; Zimmermann, N.; Hilgraf, R.; Schaffner, S.; Pfaltz, A. Adv. Synth. Catal. 2001, 343, 450; (d) Hou, D.-R.; Reibenspies, J.; Colacot, T. J.; Burgess, K. Chem. Eur. J. 2001, 7, 5391; (e) Menges, F.; Pfaltz, A. Adv. Synth. Catal. 2002, 344, 40; (f) for a review, see: Pfaltz, A.; Blankenstein, J.; Hilgraf, R.; Hörmann, E.; McIntyre, S.; Menges, F.; Schönleber, M.; Smidt, S. P.; Wüstenberg, B.; Zimmermann, N. Adv. Synth. Catal. 2003, 345, 33.
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