Copper-catalyzed reductive alkylations of enones: A novel transmetalation protocol

Angewandte Chemie - International Edition

Volumn 41, Issue 23, 2002, Pages 4580-4582

  Lipshutz, Bruce H ^a   Papa, Patrick ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Boron; Copper; Hydrides; Reduction; Transmetalation

Indexed keywords

ALKYLATION; BORON COMPOUNDS; CATALYSIS; COPPER;

TRANSMETALATION;

STEREOCHEMISTRY;

ALDEHYDE; BORANE DERIVATIVE; BORON DERIVATIVE; COPPER COMPLEX; DIHYDROCARVONE; LIGAND; METAL COMPLEX; ORGANOMETALLIC COMPOUND; SILANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; REACTION ANALYSIS; REDUCTION; THERMODYNAMICS;

EID: 0037011208     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3773(20021202)41:23<4580::AID-ANIE4580>3.0.CO;2-7     Document Type: Article

References (40)

1. B. H. Lipshutz, W. Chrisman, K. Noson, P. W. Papa, J. A. Sclafani, R. W. Vivian, J. Keith, Tetrahedron 2000, 56, 2779.
2. a) W. S. Mahoney, D. M. Brestensky, J. M. Stryker, J. Am. Chem. Soc. 1988, 110, 291;
3. b) W. S. Mahoney, J. M. Stryker, J. Am. Chem. Soc. 1989, 111, 8818; D. M. Brestensky, J. M. Stryker, Tetrahedron Lett. 1989, 30, 5677.
4. b) W. S. Mahoney, J. M. Stryker, J. Am. Chem. Soc. 1989, 111, 8818; D. M. Brestensky, J. M. Stryker, Tetrahedron Lett. 1989, 30, 5677.
5. N. J. Lawrence, M. D. D. Drew, S. M. Bushell J. Chem. Soc. Perkin Trans. 1999, 1, 3381.
6. T. Mukaiyama, K. Banno, K. Narasaka, J. Am. Chem. Soc. 1974, 96, 7503.
7. P. Wipf. Synthesis 1993, 537.
8. a) K. Miura, H. Sato, K. Tamaki, H. Ito, A. Hosomi, Tetrahedron Lett. 1997, 38, 8887;
9. b) H. Ito, T. Ishizuka, K. Arimoto, K. Miura, A. Hosomi, Tetrahedron Lett. 1997, 38, 888.
10. H. O. House, Modern Synthetic Reactions, 2nd Ed., Benjamin/Cummings. Menlo Park, CA. 1972, 145.
11. a) P. Arya, H. Qin, Tetrahedron 2000, 56, 917; C. J. Cowden, I. Paterson, Org. React. 1997, 51, 1;
12. a) P. Arya, H. Qin, Tetrahedron 2000, 56, 917; C. J. Cowden, I. Paterson, Org. React. 1997, 51, 1;
13. b) I. Paterson, C. J. Cowden, D. Wallace, Modern Carbonyl Chemistry, Wiley-VCH, Weinheim, 2000, 249.
14. a) S. Masamune, T. Sato, B. M. Kim, T. A. Wollmann, J. Am. Chem. Soc. 1986, 108, 8279;
15. b) S. Masamune, J. W. Ellingboe, W. Choy, J. Am. Chem. Soc. 1982, 104, 5526.
16. D. A. Evans, G. C. Fu, J. Org. Chem. 1990, 55, 5678.
17. G. P. Boldrini, M. Bortolotti, F. Mancini, E. Tagliavini, C. Trombini, A. Umani-Ronchi, J. Org. Chem. 1991, 56, 5820.
18. P. Knochel, P. Bhanu, S. Appana, H. Eick, J. Organomet. Chem. 1998, 562, 133.
19. Irradiation at the frequency of the resonance of the vinyl proton of the boron enolate derived from 4-hexen-3-one showed two interactions which can only exist for the Z geometry.
20. a) D. A. Evans, E. Vogel, J. V. Nelson, J. Am. Chem. Soc. 1979, 101, 6120;
21. b) D. A. Evans, V. J. Nelson, E. Vogel, J. Am. Chem. Soc. 1981, 103, 3099;
22. c) D. A. Evans, T. R. Taber, Tetrahedron Lett. 1980, 21, 4675;
23. d) S. Masamune, W. Choy, F. Kerdesky, J. Am. Chem. Soc. 1981, 103, 1566.
24. a) Aldol products uncomplicated by additional stereocenters in either coupling partner can be readily assigned on the basis of coupling constants between protons at the C-2 and C-3 sites; see D. A. Evans, J. Bartoli, T. L. Shih, J. Am. Chem. Soc. 1981, 103, 2127; L. M. Jackman, S. Sternhell, Applications of Nuclear Magnetic Resonance Spectroscopy in Organic Chemistry, 2nd Ed., Pergamon Press, Oxford, UK. 1969; b) typically, syn products show J = 3-6 Hz; c) isomers bearing an anti relationship tend to show J= 5-9 Hz.
25. a) Aldol products uncomplicated by additional stereocenters in either coupling partner can be readily assigned on the basis of coupling constants between protons at the C-2 and C-3 sites; see D. A. Evans, J. Bartoli, T. L. Shih, J. Am. Chem. Soc. 1981, 103, 2127; L. M. Jackman, S. Sternhell, Applications of Nuclear Magnetic Resonance Spectroscopy in Organic Chemistry, 2nd Ed., Pergamon Press, Oxford, UK. 1969; b) typically, syn products show J = 3-6 Hz; c) isomers bearing an anti relationship tend to show J= 5-9 Hz.
26. a) Aldol products uncomplicated by additional stereocenters in either coupling partner can be readily assigned on the basis of coupling constants between protons at the C-2 and C-3 sites; see D. A. Evans, J. Bartoli, T. L. Shih, J. Am. Chem. Soc. 1981, 103, 2127; L. M. Jackman, S. Sternhell, Applications of Nuclear Magnetic Resonance Spectroscopy in Organic Chemistry, 2nd Ed., Pergamon Press, Oxford, UK. 1969; b) typically, syn products show J = 3-6 Hz; c) isomers bearing an anti relationship tend to show J= 5-9 Hz.
27. a) Aldol products uncomplicated by additional stereocenters in either coupling partner can be readily assigned on the basis of coupling constants between protons at the C-2 and C-3 sites; see D. A. Evans, J. Bartoli, T. L. Shih, J. Am. Chem. Soc. 1981, 103, 2127; L. M. Jackman, S. Sternhell, Applications of Nuclear Magnetic Resonance Spectroscopy in Organic Chemistry, 2nd Ed., Pergamon Press, Oxford, UK. 1969; b) typically, syn products show J = 3-6 Hz; c) isomers bearing an anti relationship tend to show J= 5-9 Hz.
28. Recent Progress in the Chemical Synthesis of Antibiotics (Eds.: G. Lukacs, M. Ohno), Springer, Berlin, 1990; R. D. Norcross, I. Paterson, Chem. Rev. 1995, 95, 2041.
29. Recent Progress in the Chemical Synthesis of Antibiotics (Eds.: G. Lukacs, M. Ohno), Springer, Berlin, 1990; R. D. Norcross, I. Paterson, Chem. Rev. 1995, 95, 2041.
30. I. Paterson, M. Goodman, M. A. Lister, R. C. Schumann, C. K. McClure, R. D. Norcross, Tetrahedron 1990, 46, 4663.
31. Determined by NMR analysis of crude material to be a 9:1 mixture of anti products.
32. Confirmed via X-ray analysis.
33. J. D. Morrison, Asymmetric Synthesis, Academic Press, London, UK, 1984.
34. H. C. Brown, N. N. Joshi, J. Org. Chem. 1988, 53, 4059.
35. Y. Moritani, D. H. Appella, V. Jurkauskas, S. L. Buchwald, J. Am. Chem. Soc. 2000, 122, 6797.
36. This corresponds to a substrate: ligand (S/L) ratio of 2000:1; see ref. [22a].
37. T. Saito, T. Yokozawa, T. Ishizaki, T, Moroi, T. Miura, N. Sayo, H. Kumobayashi, Adv. Synth. Catal. 2001, 343, 264.
38. [22a] in place of dtbm-segphos under otherwise identical conditions on isophorone afforded ca, 10-20% (by TLC analysis) of the product of 1,4-reduction.
39. a) R. W. Hoffmann, K. Ditrich, Tetrahedron Lett. 1984, 25, 1781;
40. b) C. Gennari, L. Colombo, C. Scolastico, R. Todeschini, Tetrahedron 1984,40, 4051