Scope of enantioselective Palladium(II)-catalyzed aerobic alcohol oxidations with (-)-sparteine

Journal of Organic Chemistry

Volumn 68, Issue 11, 2003, Pages 4600-4603

  Mandal, Sunil K ^a   Jensen, David R ^a   Pugsley, Jacob S ^a   Sigman, Matthew S ^a  

^a UNIVERSITY OF UTAH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ENANTIOMERS;

BENZENE; CATALYSIS; OLEFINS; ORGANIC SOLVENTS; OXIDATION; PALLADIUM;

ALCOHOLS;

ALCOHOL; NATURAL PRODUCT; PALLADIUM; SPARTEINE; TERT BUTYL ALCOHOL;

ACYLATION; ARTICLE; CATALYSIS; CHEMICAL REACTION KINETICS; CHIRALITY; ENANTIOMER; ENANTIOSELECTIVITY; METHODOLOGY; OXIDATION; SYNTHESIS;

ALCOHOLS; CATALYSIS; KINETICS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PALLADIUM; SPARTEINE; STEREOISOMERISM;

EID: 0038147299     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0269161     Document Type: Article

References (61)

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9. Kinetic resolutions that have previously been accomplished by using catalytic acylation: (a) Lin, M.-H.; Rajanbabu, T. V. Org. Lett. 2002, 4, 1607 (b) Vedejs, E.; MacKay, J. A. Org. Lett. 2001, 3, 535. (c) Copeland, G. T.; Miller, S. J. J. Am. Chem. Soc. 2001, 123, 6496. (d) Bellemine-Laponnaz, S.; Tweddell, J.; Ruble, J. C.; Breitling, F. M.; Fu, G. C. Chem. Commun. 2000, 1009. (e) Jarvo, E. R.; Copeland, G. T.; Papaioannou, N.; Bonitatebus, P. J., Jr.; Miller, S. J. J. Am. Chem. Soc. 1999, 121, 11638. (f) Vedejs, E.; Daugulis, O. J. Am. Chem. Soc. 1999, 121, 5813. (g) Sano, T.; Imai, K.; Ohashi, K.; Oriyama, T. Chem. Lett. 1999, 265. (h) Miller, S. J.; Copeland, G. T.; Papaioannou, N.; Horstmann, T. E.; Ruel, E. M. J. Am. Chem. Soc. 1998, 120, 1629. (i) Ruble, J. C.; Tweddell, J.; Fu, G. C. J. Org. Chem. 1998, 63, 2794. (j) Ruble, J. C.; Latham, H. A.; Fu, G. C. J. Am. Chem. Soc. 1997, 119, 1492. (k) Kawabata, T.; Nagato, M.; Takasu, K.; Fuji, K. J. Am. Chem. Soc. 1997, 119, 3169. Using benzoylation: (l) Iwata, T.; Miyake, Y.; Nishibayashi, Y.; Uemura, S. J. Chem. Soc., Perkin. Trans. 1 2002, 154 and refs 7 and 8 cited therein.
10. Kinetic resolutions that have previously been accomplished by using catalytic acylation: (a) Lin, M.-H.; Rajanbabu, T. V. Org. Lett. 2002, 4, 1607 (b) Vedejs, E.; MacKay, J. A. Org. Lett. 2001, 3, 535. (c) Copeland, G. T.; Miller, S. J. J. Am. Chem. Soc. 2001, 123, 6496. (d) Bellemine-Laponnaz, S.; Tweddell, J.; Ruble, J. C.; Breitling, F. M.; Fu, G. C. Chem. Commun. 2000, 1009. (e) Jarvo, E. R.; Copeland, G. T.; Papaioannou, N.; Bonitatebus, P. J., Jr.; Miller, S. J. J. Am. Chem. Soc. 1999, 121, 11638. (f) Vedejs, E.; Daugulis, O. J. Am. Chem. Soc. 1999, 121, 5813. (g) Sano, T.; Imai, K.; Ohashi, K.; Oriyama, T. Chem. Lett. 1999, 265. (h) Miller, S. J.; Copeland, G. T.; Papaioannou, N.; Horstmann, T. E.; Ruel, E. M. J. Am. Chem. Soc. 1998, 120, 1629. (i) Ruble, J. C.; Tweddell, J.; Fu, G. C. J. Org. Chem. 1998, 63, 2794. (j) Ruble, J. C.; Latham, H. A.; Fu, G. C. J. Am. Chem. Soc. 1997, 119, 1492. (k) Kawabata, T.; Nagato, M.; Takasu, K.; Fuji, K. J. Am. Chem. Soc. 1997, 119, 3169. Using benzoylation: (l) Iwata, T.; Miyake, Y.; Nishibayashi, Y.; Uemura, S. J. Chem. Soc., Perkin. Trans. 1 2002, 154 and refs 7 and 8 cited therein.
11. Kinetic resolutions that have previously been accomplished by using catalytic acylation: (a) Lin, M.-H.; Rajanbabu, T. V. Org. Lett. 2002, 4, 1607 (b) Vedejs, E.; MacKay, J. A. Org. Lett. 2001, 3, 535. (c) Copeland, G. T.; Miller, S. J. J. Am. Chem. Soc. 2001, 123, 6496. (d) Bellemine-Laponnaz, S.; Tweddell, J.; Ruble, J. C.; Breitling, F. M.; Fu, G. C. Chem. Commun. 2000, 1009. (e) Jarvo, E. R.; Copeland, G. T.; Papaioannou, N.; Bonitatebus, P. J., Jr.; Miller, S. J. J. Am. Chem. Soc. 1999, 121, 11638. (f) Vedejs, E.; Daugulis, O. J. Am. Chem. Soc. 1999, 121, 5813. (g) Sano, T.; Imai, K.; Ohashi, K.; Oriyama, T. Chem. Lett. 1999, 265. (h) Miller, S. J.; Copeland, G. T.; Papaioannou, N.; Horstmann, T. E.; Ruel, E. M. J. Am. Chem. Soc. 1998, 120, 1629. (i) Ruble, J. C.; Tweddell, J.; Fu, G. C. J. Org. Chem. 1998, 63, 2794. (j) Ruble, J. C.; Latham, H. A.; Fu, G. C. J. Am. Chem. Soc. 1997, 119, 1492. (k) Kawabata, T.; Nagato, M.; Takasu, K.; Fuji, K. J. Am. Chem. Soc. 1997, 119, 3169. Using benzoylation: (l) Iwata, T.; Miyake, Y.; Nishibayashi, Y.; Uemura, S. J. Chem. Soc., Perkin. Trans. 1 2002, 154 and refs 7 and 8 cited therein.
12. Kinetic resolutions that have previously been accomplished by using catalytic acylation: (a) Lin, M.-H.; Rajanbabu, T. V. Org. Lett. 2002, 4, 1607 (b) Vedejs, E.; MacKay, J. A. Org. Lett. 2001, 3, 535. (c) Copeland, G. T.; Miller, S. J. J. Am. Chem. Soc. 2001, 123, 6496. (d) Bellemine-Laponnaz, S.; Tweddell, J.; Ruble, J. C.; Breitling, F. M.; Fu, G. C. Chem. Commun. 2000, 1009. (e) Jarvo, E. R.; Copeland, G. T.; Papaioannou, N.; Bonitatebus, P. J., Jr.; Miller, S. J. J. Am. Chem. Soc. 1999, 121, 11638. (f) Vedejs, E.; Daugulis, O. J. Am. Chem. Soc. 1999, 121, 5813. (g) Sano, T.; Imai, K.; Ohashi, K.; Oriyama, T. Chem. Lett. 1999, 265. (h) Miller, S. J.; Copeland, G. T.; Papaioannou, N.; Horstmann, T. E.; Ruel, E. M. J. Am. Chem. Soc. 1998, 120, 1629. (i) Ruble, J. C.; Tweddell, J.; Fu, G. C. J. Org. Chem. 1998, 63, 2794. (j) Ruble, J. C.; Latham, H. A.; Fu, G. C. J. Am. Chem. Soc. 1997, 119, 1492. (k) Kawabata, T.; Nagato, M.; Takasu, K.; Fuji, K. J. Am. Chem. Soc. 1997, 119, 3169. Using benzoylation: (l) Iwata, T.; Miyake, Y.; Nishibayashi, Y.; Uemura, S. J. Chem. Soc., Perkin. Trans. 1 2002, 154 and refs 7 and 8 cited therein.
13. Kinetic resolutions that have previously been accomplished by using catalytic acylation: (a) Lin, M.-H.; Rajanbabu, T. V. Org. Lett. 2002, 4, 1607 (b) Vedejs, E.; MacKay, J. A. Org. Lett. 2001, 3, 535. (c) Copeland, G. T.; Miller, S. J. J. Am. Chem. Soc. 2001, 123, 6496. (d) Bellemine-Laponnaz, S.; Tweddell, J.; Ruble, J. C.; Breitling, F. M.; Fu, G. C. Chem. Commun. 2000, 1009. (e) Jarvo, E. R.; Copeland, G. T.; Papaioannou, N.; Bonitatebus, P. J., Jr.; Miller, S. J. J. Am. Chem. Soc. 1999, 121, 11638. (f) Vedejs, E.; Daugulis, O. J. Am. Chem. Soc. 1999, 121, 5813. (g) Sano, T.; Imai, K.; Ohashi, K.; Oriyama, T. Chem. Lett. 1999, 265. (h) Miller, S. J.; Copeland, G. T.; Papaioannou, N.; Horstmann, T. E.; Ruel, E. M. J. Am. Chem. Soc. 1998, 120, 1629. (i) Ruble, J. C.; Tweddell, J.; Fu, G. C. J. Org. Chem. 1998, 63, 2794. (j) Ruble, J. C.; Latham, H. A.; Fu, G. C. J. Am. Chem. Soc. 1997, 119, 1492. (k) Kawabata, T.; Nagato, M.; Takasu, K.; Fuji, K. J. Am. Chem. Soc. 1997, 119, 3169. Using benzoylation: (l) Iwata, T.; Miyake, Y.; Nishibayashi, Y.; Uemura, S. J. Chem. Soc., Perkin. Trans. 1 2002, 154 and refs 7 and 8 cited therein.
14. Kinetic resolutions that have previously been accomplished by using catalytic acylation: (a) Lin, M.-H.; Rajanbabu, T. V. Org. Lett. 2002, 4, 1607 (b) Vedejs, E.; MacKay, J. A. Org. Lett. 2001, 3, 535. (c) Copeland, G. T.; Miller, S. J. J. Am. Chem. Soc. 2001, 123, 6496. (d) Bellemine-Laponnaz, S.; Tweddell, J.; Ruble, J. C.; Breitling, F. M.; Fu, G. C. Chem. Commun. 2000, 1009. (e) Jarvo, E. R.; Copeland, G. T.; Papaioannou, N.; Bonitatebus, P. J., Jr.; Miller, S. J. J. Am. Chem. Soc. 1999, 121, 11638. (f) Vedejs, E.; Daugulis, O. J. Am. Chem. Soc. 1999, 121, 5813. (g) Sano, T.; Imai, K.; Ohashi, K.; Oriyama, T. Chem. Lett. 1999, 265. (h) Miller, S. J.; Copeland, G. T.; Papaioannou, N.; Horstmann, T. E.; Ruel, E. M. J. Am. Chem. Soc. 1998, 120, 1629. (i) Ruble, J. C.; Tweddell, J.; Fu, G. C. J. Org. Chem. 1998, 63, 2794. (j) Ruble, J. C.; Latham, H. A.; Fu, G. C. J. Am. Chem. Soc. 1997, 119, 1492. (k) Kawabata, T.; Nagato, M.; Takasu, K.; Fuji, K. J. Am. Chem. Soc. 1997, 119, 3169. Using benzoylation: (l) Iwata, T.; Miyake, Y.; Nishibayashi, Y.; Uemura, S. J. Chem. Soc., Perkin. Trans. 1 2002, 154 and refs 7 and 8 cited therein.
15. Kinetic resolutions that have previously been accomplished by using catalytic acylation: (a) Lin, M.-H.; Rajanbabu, T. V. Org. Lett. 2002, 4, 1607 (b) Vedejs, E.; MacKay, J. A. Org. Lett. 2001, 3, 535. (c) Copeland, G. T.; Miller, S. J. J. Am. Chem. Soc. 2001, 123, 6496. (d) Bellemine-Laponnaz, S.; Tweddell, J.; Ruble, J. C.; Breitling, F. M.; Fu, G. C. Chem. Commun. 2000, 1009. (e) Jarvo, E. R.; Copeland, G. T.; Papaioannou, N.; Bonitatebus, P. J., Jr.; Miller, S. J. J. Am. Chem. Soc. 1999, 121, 11638. (f) Vedejs, E.; Daugulis, O. J. Am. Chem. Soc. 1999, 121, 5813. (g) Sano, T.; Imai, K.; Ohashi, K.; Oriyama, T. Chem. Lett. 1999, 265. (h) Miller, S. J.; Copeland, G. T.; Papaioannou, N.; Horstmann, T. E.; Ruel, E. M. J. Am. Chem. Soc. 1998, 120, 1629. (i) Ruble, J. C.; Tweddell, J.; Fu, G. C. J. Org. Chem. 1998, 63, 2794. (j) Ruble, J. C.; Latham, H. A.; Fu, G. C. J. Am. Chem. Soc. 1997, 119, 1492. (k) Kawabata, T.; Nagato, M.; Takasu, K.; Fuji, K. J. Am. Chem. Soc. 1997, 119, 3169. Using benzoylation: (l) Iwata, T.; Miyake, Y.; Nishibayashi, Y.; Uemura, S. J. Chem. Soc., Perkin. Trans. 1 2002, 154 and refs 7 and 8 cited therein.
16. Kinetic resolutions that have previously been accomplished by using catalytic acylation: (a) Lin, M.-H.; Rajanbabu, T. V. Org. Lett. 2002, 4, 1607 (b) Vedejs, E.; MacKay, J. A. Org. Lett. 2001, 3, 535. (c) Copeland, G. T.; Miller, S. J. J. Am. Chem. Soc. 2001, 123, 6496. (d) Bellemine-Laponnaz, S.; Tweddell, J.; Ruble, J. C.; Breitling, F. M.; Fu, G. C. Chem. Commun. 2000, 1009. (e) Jarvo, E. R.; Copeland, G. T.; Papaioannou, N.; Bonitatebus, P. J., Jr.; Miller, S. J. J. Am. Chem. Soc. 1999, 121, 11638. (f) Vedejs, E.; Daugulis, O. J. Am. Chem. Soc. 1999, 121, 5813. (g) Sano, T.; Imai, K.; Ohashi, K.; Oriyama, T. Chem. Lett. 1999, 265. (h) Miller, S. J.; Copeland, G. T.; Papaioannou, N.; Horstmann, T. E.; Ruel, E. M. J. Am. Chem. Soc. 1998, 120, 1629. (i) Ruble, J. C.; Tweddell, J.; Fu, G. C. J. Org. Chem. 1998, 63, 2794. (j) Ruble, J. C.; Latham, H. A.; Fu, G. C. J. Am. Chem. Soc. 1997, 119, 1492. (k) Kawabata, T.; Nagato, M.; Takasu, K.; Fuji, K. J. Am. Chem. Soc. 1997, 119, 3169. Using benzoylation: (l) Iwata, T.; Miyake, Y.; Nishibayashi, Y.; Uemura, S. J. Chem. Soc., Perkin. Trans. 1 2002, 154 and refs 7 and 8 cited therein.
17. Kinetic resolutions that have previously been accomplished by using catalytic acylation: (a) Lin, M.-H.; Rajanbabu, T. V. Org. Lett. 2002, 4, 1607 (b) Vedejs, E.; MacKay, J. A. Org. Lett. 2001, 3, 535. (c) Copeland, G. T.; Miller, S. J. J. Am. Chem. Soc. 2001, 123, 6496. (d) Bellemine-Laponnaz, S.; Tweddell, J.; Ruble, J. C.; Breitling, F. M.; Fu, G. C. Chem. Commun. 2000, 1009. (e) Jarvo, E. R.; Copeland, G. T.; Papaioannou, N.; Bonitatebus, P. J., Jr.; Miller, S. J. J. Am. Chem. Soc. 1999, 121, 11638. (f) Vedejs, E.; Daugulis, O. J. Am. Chem. Soc. 1999, 121, 5813. (g) Sano, T.; Imai, K.; Ohashi, K.; Oriyama, T. Chem. Lett. 1999, 265. (h) Miller, S. J.; Copeland, G. T.; Papaioannou, N.; Horstmann, T. E.; Ruel, E. M. J. Am. Chem. Soc. 1998, 120, 1629. (i) Ruble, J. C.; Tweddell, J.; Fu, G. C. J. Org. Chem. 1998, 63, 2794. (j) Ruble, J. C.; Latham, H. A.; Fu, G. C. J. Am. Chem. Soc. 1997, 119, 1492. (k) Kawabata, T.; Nagato, M.; Takasu, K.; Fuji, K. J. Am. Chem. Soc. 1997, 119, 3169. Using benzoylation: (l) Iwata, T.; Miyake, Y.; Nishibayashi, Y.; Uemura, S. J. Chem. Soc., Perkin. Trans. 1 2002, 154 and refs 7 and 8 cited therein.
18. Kinetic resolutions that have previously been accomplished by using catalytic acylation: (a) Lin, M.-H.; Rajanbabu, T. V. Org. Lett. 2002, 4, 1607 (b) Vedejs, E.; MacKay, J. A. Org. Lett. 2001, 3, 535. (c) Copeland, G. T.; Miller, S. J. J. Am. Chem. Soc. 2001, 123, 6496. (d) Bellemine-Laponnaz, S.; Tweddell, J.; Ruble, J. C.; Breitling, F. M.; Fu, G. C. Chem. Commun. 2000, 1009. (e) Jarvo, E. R.; Copeland, G. T.; Papaioannou, N.; Bonitatebus, P. J., Jr.; Miller, S. J. J. Am. Chem. Soc. 1999, 121, 11638. (f) Vedejs, E.; Daugulis, O. J. Am. Chem. Soc. 1999, 121, 5813. (g) Sano, T.; Imai, K.; Ohashi, K.; Oriyama, T. Chem. Lett. 1999, 265. (h) Miller, S. J.; Copeland, G. T.; Papaioannou, N.; Horstmann, T. E.; Ruel, E. M. J. Am. Chem. Soc. 1998, 120, 1629. (i) Ruble, J. C.; Tweddell, J.; Fu, G. C. J. Org. Chem. 1998, 63, 2794. (j) Ruble, J. C.; Latham, H. A.; Fu, G. C. J. Am. Chem. Soc. 1997, 119, 1492. (k) Kawabata, T.; Nagato, M.; Takasu, K.; Fuji, K. J. Am. Chem. Soc. 1997, 119, 3169. Using benzoylation: (l) Iwata, T.; Miyake, Y.; Nishibayashi, Y.; Uemura, S. J. Chem. Soc., Perkin. Trans. 1 2002, 154 and refs 7 and 8 cited therein.
19. Kinetic resolutions that have previously been accomplished by using catalytic acylation: (a) Lin, M.-H.; Rajanbabu, T. V. Org. Lett. 2002, 4, 1607 (b) Vedejs, E.; MacKay, J. A. Org. Lett. 2001, 3, 535. (c) Copeland, G. T.; Miller, S. J. J. Am. Chem. Soc. 2001, 123, 6496. (d) Bellemine-Laponnaz, S.; Tweddell, J.; Ruble, J. C.; Breitling, F. M.; Fu, G. C. Chem. Commun. 2000, 1009. (e) Jarvo, E. R.; Copeland, G. T.; Papaioannou, N.; Bonitatebus, P. J., Jr.; Miller, S. J. J. Am. Chem. Soc. 1999, 121, 11638. (f) Vedejs, E.; Daugulis, O. J. Am. Chem. Soc. 1999, 121, 5813. (g) Sano, T.; Imai, K.; Ohashi, K.; Oriyama, T. Chem. Lett. 1999, 265. (h) Miller, S. J.; Copeland, G. T.; Papaioannou, N.; Horstmann, T. E.; Ruel, E. M. J. Am. Chem. Soc. 1998, 120, 1629. (i) Ruble, J. C.; Tweddell, J.; Fu, G. C. J. Org. Chem. 1998, 63, 2794. (j) Ruble, J. C.; Latham, H. A.; Fu, G. C. J. Am. Chem. Soc. 1997, 119, 1492. (k) Kawabata, T.; Nagato, M.; Takasu, K.; Fuji, K. J. Am. Chem. Soc. 1997, 119, 3169. Using benzoylation: (l) Iwata, T.; Miyake, Y.; Nishibayashi, Y.; Uemura, S. J. Chem. Soc., Perkin. Trans. 1 2002, 154 and refs 7 and 8 cited therein.
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32. For examples of Pd(II)-catalyzed aerobic oxidations, see: (a) Schultz, M. J.; Park, C.; Sigman, M. S. Chem. Commun. 2002, 3034-3035. (b) Ten Brink, G.-J.; Arends, I. W. C. E.; Sheldon, R. A. Adv. Synth. Catal. 2002, 344, 355-369. (c) Kakiuchi, N.; Maeda, Y.; Nishimura, T.; Uemura S. J. Org. Chem. 2001, 66, 6620. (d) ten Brink, G.-J.; Arends, I. W. C. E.; Sheldon, R. A. Science 2000, 287, 1636. (e) Peterson, K. P.; Larock, R. C. J. Org. Chem. 1998, 62, 3185. (f) Kaneda, K.; Fujii, M.; Morioka, K. J. Org. Chem. 1996, 61, 4502. (g) Gomez-Bengoa, E.; Noheda, P.; Echavarren, A. M. Tetrahedron Lett. 1994, 35, 7097. (h) Blackburn, T. F.; Schwartz, J. J. Chem. Soc., Chem. Commun. 1977, 157.
33. For examples of Pd(II)-catalyzed aerobic oxidations, see: (a) Schultz, M. J.; Park, C.; Sigman, M. S. Chem. Commun. 2002, 3034-3035. (b) Ten Brink, G.-J.; Arends, I. W. C. E.; Sheldon, R. A. Adv. Synth. Catal. 2002, 344, 355-369. (c) Kakiuchi, N.; Maeda, Y.; Nishimura, T.; Uemura S. J. Org. Chem. 2001, 66, 6620. (d) ten Brink, G.-J.; Arends, I. W. C. E.; Sheldon, R. A. Science 2000, 287, 1636. (e) Peterson, K. P.; Larock, R. C. J. Org. Chem. 1998, 62, 3185. (f) Kaneda, K.; Fujii, M.; Morioka, K. J. Org. Chem. 1996, 61, 4502. (g) Gomez-Bengoa, E.; Noheda, P.; Echavarren, A. M. Tetrahedron Lett. 1994, 35, 7097. (h) Blackburn, T. F.; Schwartz, J. J. Chem. Soc., Chem. Commun. 1977, 157.
34. For examples of Pd(II)-catalyzed aerobic oxidations, see: (a) Schultz, M. J.; Park, C.; Sigman, M. S. Chem. Commun. 2002, 3034-3035. (b) Ten Brink, G.-J.; Arends, I. W. C. E.; Sheldon, R. A. Adv. Synth. Catal. 2002, 344, 355-369. (c) Kakiuchi, N.; Maeda, Y.; Nishimura, T.; Uemura S. J. Org. Chem. 2001, 66, 6620. (d) ten Brink, G.-J.; Arends, I. W. C. E.; Sheldon, R. A. Science 2000, 287, 1636. (e) Peterson, K. P.; Larock, R. C. J. Org. Chem. 1998, 62, 3185. (f) Kaneda, K.; Fujii, M.; Morioka, K. J. Org. Chem. 1996, 61, 4502. (g) Gomez-Bengoa, E.; Noheda, P.; Echavarren, A. M. Tetrahedron Lett. 1994, 35, 7097. (h) Blackburn, T. F.; Schwartz, J. J. Chem. Soc., Chem. Commun. 1977, 157.
35. For examples of Pd(II)-catalyzed aerobic oxidations, see: (a) Schultz, M. J.; Park, C.; Sigman, M. S. Chem. Commun. 2002, 3034-3035. (b) Ten Brink, G.-J.; Arends, I. W. C. E.; Sheldon, R. A. Adv. Synth. Catal. 2002, 344, 355-369. (c) Kakiuchi, N.; Maeda, Y.; Nishimura, T.; Uemura S. J. Org. Chem. 2001, 66, 6620. (d) ten Brink, G.-J.; Arends, I. W. C. E.; Sheldon, R. A. Science 2000, 287, 1636. (e) Peterson, K. P.; Larock, R. C. J. Org. Chem. 1998, 62, 3185. (f) Kaneda, K.; Fujii, M.; Morioka, K. J. Org. Chem. 1996, 61, 4502. (g) Gomez-Bengoa, E.; Noheda, P.; Echavarren, A. M. Tetrahedron Lett. 1994, 35, 7097. (h) Blackburn, T. F.; Schwartz, J. J. Chem. Soc., Chem. Commun. 1977, 157.
36. For examples of Pd(II)-catalyzed aerobic oxidations, see: (a) Schultz, M. J.; Park, C.; Sigman, M. S. Chem. Commun. 2002, 3034-3035. (b) Ten Brink, G.-J.; Arends, I. W. C. E.; Sheldon, R. A. Adv. Synth. Catal. 2002, 344, 355-369. (c) Kakiuchi, N.; Maeda, Y.; Nishimura, T.; Uemura S. J. Org. Chem. 2001, 66, 6620. (d) ten Brink, G.-J.; Arends, I. W. C. E.; Sheldon, R. A. Science 2000, 287, 1636. (e) Peterson, K. P.; Larock, R. C. J. Org. Chem. 1998, 62, 3185. (f) Kaneda, K.; Fujii, M.; Morioka, K. J. Org. Chem. 1996, 61, 4502. (g) Gomez-Bengoa, E.; Noheda, P.; Echavarren, A. M. Tetrahedron Lett. 1994, 35, 7097. (h) Blackburn, T. F.; Schwartz, J. J. Chem. Soc., Chem. Commun. 1977, 157.
37. For examples of Pd(II)-catalyzed aerobic oxidations, see: (a) Schultz, M. J.; Park, C.; Sigman, M. S. Chem. Commun. 2002, 3034-3035. (b) Ten Brink, G.-J.; Arends, I. W. C. E.; Sheldon, R. A. Adv. Synth. Catal. 2002, 344, 355-369. (c) Kakiuchi, N.; Maeda, Y.; Nishimura, T.; Uemura S. J. Org. Chem. 2001, 66, 6620. (d) ten Brink, G.-J.; Arends, I. W. C. E.; Sheldon, R. A. Science 2000, 287, 1636. (e) Peterson, K. P.; Larock, R. C. J. Org. Chem. 1998, 62, 3185. (f) Kaneda, K.; Fujii, M.; Morioka, K. J. Org. Chem. 1996, 61, 4502. (g) Gomez-Bengoa, E.; Noheda, P.; Echavarren, A. M. Tetrahedron Lett. 1994, 35, 7097. (h) Blackburn, T. F.; Schwartz, J. J. Chem. Soc., Chem. Commun. 1977, 157.
38. For examples of Pd(II)-catalyzed aerobic oxidations, see: (a) Schultz, M. J.; Park, C.; Sigman, M. S. Chem. Commun. 2002, 3034-3035. (b) Ten Brink, G.-J.; Arends, I. W. C. E.; Sheldon, R. A. Adv. Synth. Catal. 2002, 344, 355-369. (c) Kakiuchi, N.; Maeda, Y.; Nishimura, T.; Uemura S. J. Org. Chem. 2001, 66, 6620. (d) ten Brink, G.-J.; Arends, I. W. C. E.; Sheldon, R. A. Science 2000, 287, 1636. (e) Peterson, K. P.; Larock, R. C. J. Org. Chem. 1998, 62, 3185. (f) Kaneda, K.; Fujii, M.; Morioka, K. J. Org. Chem. 1996, 61, 4502. (g) Gomez-Bengoa, E.; Noheda, P.; Echavarren, A. M. Tetrahedron Lett. 1994, 35, 7097. (h) Blackburn, T. F.; Schwartz, J. J. Chem. Soc., Chem. Commun. 1977, 157.
39. (a) Nishimura, T.; Onoue, T.; Ohe, K.; Uemura, S. J. Org. Chem. 1999, 64, 6750.
40. (b) Nishimura, T.; Onoue, T.; Ohe, K.; Uemura, S. Tetrahedron Lett. 1998, 39, 6011.
41. Sudalai, A.; Ali, I. S. Tetrahedron Lett. 2002, 43, 5435.
42. See Supporting Information for details.
43. 2 formed in the reaction, see ref 10a. We also found that addition of a drop of water to the reaction mixture inhibits the reaction.
44. For an example of Vanadium-catalyzed aerobic oxidations of propargylic alcohols, see: Maeda, Y.; Kakiuchi, N.; Matsumura, S.; Nishimura, T.; Kawamura, T.; Uemura, S. J. Org. Chem. 2002, 67, 6718-6724.
45. For examples of nonenzymatic desymmetrization of meso-diols see: (a) Trost, B. M.; Mino, T. J. Am. Chem. Soc. 2003, 125, 2410. (b) Hodgson, R.; Majid, T.; Nelson, A. J. Chem. Soc., Perkin Trans. 1 2002, 14, 1631-1643. (c) Jiang, L.; Burke, S. D. Org. Lett. 2002, 4, 3411-3414. (d) Harada, T.; Sekiguchi, K.; Nakamura, T.; Suzuki, J.; Oku, A. Org. Lett. 2001, 3, 3309-3312. (e) Harada, T.; Yamanaka, H.; Oku, A. Synlett 2001, 1, 61-64. (f) Yamada, S.; Katsumata, H. J. Org. Chem. 1999, 64, 9365. (g) Oriyama, T.; Imai, K.; Hosoya, T.; Sano, T. Tetrahedron Lett. 1998, 39, 397. (h) Via acetal cleavage, see: Fujioka, H.; Nagatomi, Y.; Kotoku, N.; Kitagawa, H. Tetrahedron 2000, 56, 10141. (i) Kinugasa, M.; Harada, T.; Oku, A. J. Am. Chem. Soc. 1997, 119, 9067.
46. For examples of nonenzymatic desymmetrization of meso-diols see: (a) Trost, B. M.; Mino, T. J. Am. Chem. Soc. 2003, 125, 2410. (b) Hodgson, R.; Majid, T.; Nelson, A. J. Chem. Soc., Perkin Trans. 1 2002, 14, 1631-1643. (c) Jiang, L.; Burke, S. D. Org. Lett. 2002, 4, 3411-3414. (d) Harada, T.; Sekiguchi, K.; Nakamura, T.; Suzuki, J.; Oku, A. Org. Lett. 2001, 3, 3309-3312. (e) Harada, T.; Yamanaka, H.; Oku, A. Synlett 2001, 1, 61-64. (f) Yamada, S.; Katsumata, H. J. Org. Chem. 1999, 64, 9365. (g) Oriyama, T.; Imai, K.; Hosoya, T.; Sano, T. Tetrahedron Lett. 1998, 39, 397. (h) Via acetal cleavage, see: Fujioka, H.; Nagatomi, Y.; Kotoku, N.; Kitagawa, H. Tetrahedron 2000, 56, 10141. (i) Kinugasa, M.; Harada, T.; Oku, A. J. Am. Chem. Soc. 1997, 119, 9067.
47. For examples of nonenzymatic desymmetrization of meso-diols see: (a) Trost, B. M.; Mino, T. J. Am. Chem. Soc. 2003, 125, 2410. (b) Hodgson, R.; Majid, T.; Nelson, A. J. Chem. Soc., Perkin Trans. 1 2002, 14, 1631-1643. (c) Jiang, L.; Burke, S. D. Org. Lett. 2002, 4, 3411-3414. (d) Harada, T.; Sekiguchi, K.; Nakamura, T.; Suzuki, J.; Oku, A. Org. Lett. 2001, 3, 3309-3312. (e) Harada, T.; Yamanaka, H.; Oku, A. Synlett 2001, 1, 61-64. (f) Yamada, S.; Katsumata, H. J. Org. Chem. 1999, 64, 9365. (g) Oriyama, T.; Imai, K.; Hosoya, T.; Sano, T. Tetrahedron Lett. 1998, 39, 397. (h) Via acetal cleavage, see: Fujioka, H.; Nagatomi, Y.; Kotoku, N.; Kitagawa, H. Tetrahedron 2000, 56, 10141. (i) Kinugasa, M.; Harada, T.; Oku, A. J. Am. Chem. Soc. 1997, 119, 9067.
48. For examples of nonenzymatic desymmetrization of meso-diols see: (a) Trost, B. M.; Mino, T. J. Am. Chem. Soc. 2003, 125, 2410. (b) Hodgson, R.; Majid, T.; Nelson, A. J. Chem. Soc., Perkin Trans. 1 2002, 14, 1631-1643. (c) Jiang, L.; Burke, S. D. Org. Lett. 2002, 4, 3411-3414. (d) Harada, T.; Sekiguchi, K.; Nakamura, T.; Suzuki, J.; Oku, A. Org. Lett. 2001, 3, 3309-3312. (e) Harada, T.; Yamanaka, H.; Oku, A. Synlett 2001, 1, 61-64. (f) Yamada, S.; Katsumata, H. J. Org. Chem. 1999, 64, 9365. (g) Oriyama, T.; Imai, K.; Hosoya, T.; Sano, T. Tetrahedron Lett. 1998, 39, 397. (h) Via acetal cleavage, see: Fujioka, H.; Nagatomi, Y.; Kotoku, N.; Kitagawa, H. Tetrahedron 2000, 56, 10141. (i) Kinugasa, M.; Harada, T.; Oku, A. J. Am. Chem. Soc. 1997, 119, 9067.
49. For examples of nonenzymatic desymmetrization of meso-diols see: (a) Trost, B. M.; Mino, T. J. Am. Chem. Soc. 2003, 125, 2410. (b) Hodgson, R.; Majid, T.; Nelson, A. J. Chem. Soc., Perkin Trans. 1 2002, 14, 1631-1643. (c) Jiang, L.; Burke, S. D. Org. Lett. 2002, 4, 3411-3414. (d) Harada, T.; Sekiguchi, K.; Nakamura, T.; Suzuki, J.; Oku, A. Org. Lett. 2001, 3, 3309-3312. (e) Harada, T.; Yamanaka, H.; Oku, A. Synlett 2001, 1, 61-64. (f) Yamada, S.; Katsumata, H. J. Org. Chem. 1999, 64, 9365. (g) Oriyama, T.; Imai, K.; Hosoya, T.; Sano, T. Tetrahedron Lett. 1998, 39, 397. (h) Via acetal cleavage, see: Fujioka, H.; Nagatomi, Y.; Kotoku, N.; Kitagawa, H. Tetrahedron 2000, 56, 10141. (i) Kinugasa, M.; Harada, T.; Oku, A. J. Am. Chem. Soc. 1997, 119, 9067.
50. For examples of nonenzymatic desymmetrization of meso-diols see: (a) Trost, B. M.; Mino, T. J. Am. Chem. Soc. 2003, 125, 2410. (b) Hodgson, R.; Majid, T.; Nelson, A. J. Chem. Soc., Perkin Trans. 1 2002, 14, 1631-1643. (c) Jiang, L.; Burke, S. D. Org. Lett. 2002, 4, 3411-3414. (d) Harada, T.; Sekiguchi, K.; Nakamura, T.; Suzuki, J.; Oku, A. Org. Lett. 2001, 3, 3309-3312. (e) Harada, T.; Yamanaka, H.; Oku, A. Synlett 2001, 1, 61-64. (f) Yamada, S.; Katsumata, H. J. Org. Chem. 1999, 64, 9365. (g) Oriyama, T.; Imai, K.; Hosoya, T.; Sano, T. Tetrahedron Lett. 1998, 39, 397. (h) Via acetal cleavage, see: Fujioka, H.; Nagatomi, Y.; Kotoku, N.; Kitagawa, H. Tetrahedron 2000, 56, 10141. (i) Kinugasa, M.; Harada, T.; Oku, A. J. Am. Chem. Soc. 1997, 119, 9067.
51. For examples of nonenzymatic desymmetrization of meso-diols see: (a) Trost, B. M.; Mino, T. J. Am. Chem. Soc. 2003, 125, 2410. (b) Hodgson, R.; Majid, T.; Nelson, A. J. Chem. Soc., Perkin Trans. 1 2002, 14, 1631-1643. (c) Jiang, L.; Burke, S. D. Org. Lett. 2002, 4, 3411-3414. (d) Harada, T.; Sekiguchi, K.; Nakamura, T.; Suzuki, J.; Oku, A. Org. Lett. 2001, 3, 3309-3312. (e) Harada, T.; Yamanaka, H.; Oku, A. Synlett 2001, 1, 61-64. (f) Yamada, S.; Katsumata, H. J. Org. Chem. 1999, 64, 9365. (g) Oriyama, T.; Imai, K.; Hosoya, T.; Sano, T. Tetrahedron Lett. 1998, 39, 397. (h) Via acetal cleavage, see: Fujioka, H.; Nagatomi, Y.; Kotoku, N.; Kitagawa, H. Tetrahedron 2000, 56, 10141. (i) Kinugasa, M.; Harada, T.; Oku, A. J. Am. Chem. Soc. 1997, 119, 9067.
52. For examples of nonenzymatic desymmetrization of meso-diols see: (a) Trost, B. M.; Mino, T. J. Am. Chem. Soc. 2003, 125, 2410. (b) Hodgson, R.; Majid, T.; Nelson, A. J. Chem. Soc., Perkin Trans. 1 2002, 14, 1631-1643. (c) Jiang, L.; Burke, S. D. Org. Lett. 2002, 4, 3411-3414. (d) Harada, T.; Sekiguchi, K.; Nakamura, T.; Suzuki, J.; Oku, A. Org. Lett. 2001, 3, 3309-3312. (e) Harada, T.; Yamanaka, H.; Oku, A. Synlett 2001, 1, 61-64. (f) Yamada, S.; Katsumata, H. J. Org. Chem. 1999, 64, 9365. (g) Oriyama, T.; Imai, K.; Hosoya, T.; Sano, T. Tetrahedron Lett. 1998, 39, 397. (h) Via acetal cleavage, see: Fujioka, H.; Nagatomi, Y.; Kotoku, N.; Kitagawa, H. Tetrahedron 2000, 56, 10141. (i) Kinugasa, M.; Harada, T.; Oku, A. J. Am. Chem. Soc. 1997, 119, 9067.
53. For examples of nonenzymatic desymmetrization of meso-diols see: (a) Trost, B. M.; Mino, T. J. Am. Chem. Soc. 2003, 125, 2410. (b) Hodgson, R.; Majid, T.; Nelson, A. J. Chem. Soc., Perkin Trans. 1 2002, 14, 1631-1643. (c) Jiang, L.; Burke, S. D. Org. Lett. 2002, 4, 3411-3414. (d) Harada, T.; Sekiguchi, K.; Nakamura, T.; Suzuki, J.; Oku, A. Org. Lett. 2001, 3, 3309-3312. (e) Harada, T.; Yamanaka, H.; Oku, A. Synlett 2001, 1, 61-64. (f) Yamada, S.; Katsumata, H. J. Org. Chem. 1999, 64, 9365. (g) Oriyama, T.; Imai, K.; Hosoya, T.; Sano, T. Tetrahedron Lett. 1998, 39, 397. (h) Via acetal cleavage, see: Fujioka, H.; Nagatomi, Y.; Kotoku, N.; Kitagawa, H. Tetrahedron 2000, 56, 10141. (i) Kinugasa, M.; Harada, T.; Oku, A. J. Am. Chem. Soc. 1997, 119, 9067.
54. For a recent review, see: Machajewski, T. D.; Wong, C.-H.; Lerner, R. A. Angew. Chem., Int. Ed. 2000, 39, 1352.
55. For a review of catalytic asymmetric Mukaiyama aldol reactions, see: Carreira, E. M. Comput. Asym. Catal. 1999, I-III, 997.
56. (a) Mueller, J. A.; Jensen, D. R.; Sigman, M. S. J. Am. Chem. Soc. 2002, 124, 8202-8203.
57. (b) Mueller, J. A.; Sigman, M. S. J. Am. Chem. Soc., in press.
58. These observations do not rule out the possibility that tert-butyl alcohol transiently interacts with the catalyst.
59. Smith, B. T.; Wendt, J. A.; Aube, J. Org. Lett. 2002, 4, 2577-2579.
60. Dearden, M. J.; Firkin, C. R.; Hermet, J.-P. R.; O'Brien, P. J. Am. Chem. Soc. 2002, 124, 11870-11871.
61. Jensen, D. R.; Sigman, M. S. Org. Lett. 2003, 5, 63-65.