Radical α-C-H hydroxyalkylation of ethers and acetal

Journal of Organic Chemistry

Volumn 70, Issue 6, 2005, Pages 2342-2345

  Yoshimitsu, Takehiko ^a   Arano, Yoshimasa ^a   Nagaoka, Hiroto ^a  

^a MEIJI PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; ALDEHYDES; ETHERS;

ACETALS; HYDROXYALKYLATION; INTERMOLECULAR ADDITION; OXYGEN-CONTAINING COMPOUNDS;

ALKYLATION;

ACETAL; CARBON; HYDROGEN; OXYGEN;

ALKYLATION; ARTICLE; HYDRATION;

ACETALS; ALKYLATION; ETHERS; FREE RADICALS; MOLECULAR CONFORMATION;

EID: 15444361899     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo048248k     Document Type: Article

References (71)

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31. Pioneering studies in this area include: (a) Jacobs, R. L.; Ecke, G. G. J. Org. Chem. 1963, 28, 3036-3038. (b) Dieckmann, J.; Pedersen, C. J. J. Chem. 1964, 29, 2031-2032. (c) Rosenthal, I.; Elad, D. Tetrahedron 1967, 23, 3193-3204. (d) Muramatsu, H.; Inukai, K.; Ueda, T. J. Org. Chem. 1964, 29, 2220-2223. (e) Citterio, A.; Arnoldi, A.; Griffini, A. Tetrahedron 1982, 38, 393-395. (f) Matthews, D. P.; McCarthy, J. R. J. Org. Chem. 1990, 55, 2973-2975. (g) Minisci, F.; Citterio, A.; Vismara, E.; Giordano, C. Tetrahedron 1985, 41, 4157-4170. (h) Crabtree, R. H. Pure Appl. Chem. 1995, 67, 39-45. (i) Brown, S. H.; Crabtree, R. H. J. Am. Chem. Soc. 1989, 111, 2935-2946. Reviews containing a brief discussion on this topic include: (j) Walling, C.; Huyser, E. S. Org. React. 1963, 13, 91-149. (k) Abell, P. I. In Free Radicals; Kochi, J. K.,Ed.; Wiley-Interscience: New York, 1973; Vol. 2, p 63. (l) Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds; Pergamon Press: Oxford, UK, 1986.
32. Pioneering studies in this area include: (a) Jacobs, R. L.; Ecke, G. G. J. Org. Chem. 1963, 28, 3036-3038. (b) Dieckmann, J.; Pedersen, C. J. J. Chem. 1964, 29, 2031-2032. (c) Rosenthal, I.; Elad, D. Tetrahedron 1967, 23, 3193-3204. (d) Muramatsu, H.; Inukai, K.; Ueda, T. J. Org. Chem. 1964, 29, 2220-2223. (e) Citterio, A.; Arnoldi, A.; Griffini, A. Tetrahedron 1982, 38, 393-395. (f) Matthews, D. P.; McCarthy, J. R. J. Org. Chem. 1990, 55, 2973-2975. (g) Minisci, F.; Citterio, A.; Vismara, E.; Giordano, C. Tetrahedron 1985, 41, 4157-4170. (h) Crabtree, R. H. Pure Appl. Chem. 1995, 67, 39-45. (i) Brown, S. H.; Crabtree, R. H. J. Am. Chem. Soc. 1989, 111, 2935-2946. Reviews containing a brief discussion on this topic include: (j) Walling, C.; Huyser, E. S. Org. React. 1963, 13, 91-149. (k) Abell, P. I. In Free Radicals; Kochi, J. K.,Ed.; Wiley-Interscience: New York, 1973; Vol. 2, p 63. (l) Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds; Pergamon Press: Oxford, UK, 1986.
33. Pioneering studies in this area include: (a) Jacobs, R. L.; Ecke, G. G. J. Org. Chem. 1963, 28, 3036-3038. (b) Dieckmann, J.; Pedersen, C. J. J. Chem. 1964, 29, 2031-2032. (c) Rosenthal, I.; Elad, D. Tetrahedron 1967, 23, 3193-3204. (d) Muramatsu, H.; Inukai, K.; Ueda, T. J. Org. Chem. 1964, 29, 2220-2223. (e) Citterio, A.; Arnoldi, A.; Griffini, A. Tetrahedron 1982, 38, 393-395. (f) Matthews, D. P.; McCarthy, J. R. J. Org. Chem. 1990, 55, 2973-2975. (g) Minisci, F.; Citterio, A.; Vismara, E.; Giordano, C. Tetrahedron 1985, 41, 4157-4170. (h) Crabtree, R. H. Pure Appl. Chem. 1995, 67, 39-45. (i) Brown, S. H.; Crabtree, R. H. J. Am. Chem. Soc. 1989, 111, 2935-2946. Reviews containing a brief discussion on this topic include: (j) Walling, C.; Huyser, E. S. Org. React. 1963, 13, 91-149. (k) Abell, P. I. In Free Radicals; Kochi, J. K.,Ed.; Wiley-Interscience: New York, 1973; Vol. 2, p 63. (l) Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds; Pergamon Press: Oxford, UK, 1986.
34. Pioneering studies in this area include: (a) Jacobs, R. L.; Ecke, G. G. J. Org. Chem. 1963, 28, 3036-3038. (b) Dieckmann, J.; Pedersen, C. J. J. Chem. 1964, 29, 2031-2032. (c) Rosenthal, I.; Elad, D. Tetrahedron 1967, 23, 3193-3204. (d) Muramatsu, H.; Inukai, K.; Ueda, T. J. Org. Chem. 1964, 29, 2220-2223. (e) Citterio, A.; Arnoldi, A.; Griffini, A. Tetrahedron 1982, 38, 393-395. (f) Matthews, D. P.; McCarthy, J. R. J. Org. Chem. 1990, 55, 2973-2975. (g) Minisci, F.; Citterio, A.; Vismara, E.; Giordano, C. Tetrahedron 1985, 41, 4157-4170. (h) Crabtree, R. H. Pure Appl. Chem. 1995, 67, 39-45. (i) Brown, S. H.; Crabtree, R. H. J. Am. Chem. Soc. 1989, 111, 2935-2946. Reviews containing a brief discussion on this topic include: (j) Walling, C.; Huyser, E. S. Org. React. 1963, 13, 91-149. (k) Abell, P. I. In Free Radicals; Kochi, J. K.,Ed.; Wiley-Interscience: New York, 1973; Vol. 2, p 63. (l) Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds; Pergamon Press: Oxford, UK, 1986.
35. Pioneering studies in this area include: (a) Jacobs, R. L.; Ecke, G. G. J. Org. Chem. 1963, 28, 3036-3038. (b) Dieckmann, J.; Pedersen, C. J. J. Chem. 1964, 29, 2031-2032. (c) Rosenthal, I.; Elad, D. Tetrahedron 1967, 23, 3193-3204. (d) Muramatsu, H.; Inukai, K.; Ueda, T. J. Org. Chem. 1964, 29, 2220-2223. (e) Citterio, A.; Arnoldi, A.; Griffini, A. Tetrahedron 1982, 38, 393-395. (f) Matthews, D. P.; McCarthy, J. R. J. Org. Chem. 1990, 55, 2973-2975. (g) Minisci, F.; Citterio, A.; Vismara, E.; Giordano, C. Tetrahedron 1985, 41, 4157-4170. (h) Crabtree, R. H. Pure Appl. Chem. 1995, 67, 39-45. (i) Brown, S. H.; Crabtree, R. H. J. Am. Chem. Soc. 1989, 111, 2935-2946. Reviews containing a brief discussion on this topic include: (j) Walling, C.; Huyser, E. S. Org. React. 1963, 13, 91-149. (k) Abell, P. I. In Free Radicals; Kochi, J. K.,Ed.; Wiley-Interscience: New York, 1973; Vol. 2, p 63. (l) Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds; Pergamon Press: Oxford, UK, 1986.
36. Pioneering studies in this area include: (a) Jacobs, R. L.; Ecke, G. G. J. Org. Chem. 1963, 28, 3036-3038. (b) Dieckmann, J.; Pedersen, C. J. J. Chem. 1964, 29, 2031-2032. (c) Rosenthal, I.; Elad, D. Tetrahedron 1967, 23, 3193-3204. (d) Muramatsu, H.; Inukai, K.; Ueda, T. J. Org. Chem. 1964, 29, 2220-2223. (e) Citterio, A.; Arnoldi, A.; Griffini, A. Tetrahedron 1982, 38, 393-395. (f) Matthews, D. P.; McCarthy, J. R. J. Org. Chem. 1990, 55, 2973-2975. (g) Minisci, F.; Citterio, A.; Vismara, E.; Giordano, C. Tetrahedron 1985, 41, 4157-4170. (h) Crabtree, R. H. Pure Appl. Chem. 1995, 67, 39-45. (i) Brown, S. H.; Crabtree, R. H. J. Am. Chem. Soc. 1989, 111, 2935-2946. Reviews containing a brief discussion on this topic include: (j) Walling, C.; Huyser, E. S. Org. React. 1963, 13, 91-149. (k) Abell, P. I. In Free Radicals; Kochi, J. K.,Ed.; Wiley-Interscience: New York, 1973; Vol. 2, p 63. (1) Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds; Pergamon Press: Oxford, UK, 1986.
37. Pioneering studies in this area include: (a) Jacobs, R. L.; Ecke, G. G. J. Org. Chem. 1963, 28, 3036-3038. (b) Dieckmann, J.; Pedersen, C. J. J. Chem. 1964, 29, 2031-2032. (c) Rosenthal, I.; Elad, D. Tetrahedron 1967, 23, 3193-3204. (d) Muramatsu, H.; Inukai, K.; Ueda, T. J. Org. Chem. 1964, 29, 2220-2223. (e) Citterio, A.; Arnoldi, A.; Griffini, A. Tetrahedron 1982, 38, 393-395. (f) Matthews, D. P.; McCarthy, J. R. J. Org. Chem. 1990, 55, 2973-2975. (g) Minisci, F.; Citterio, A.; Vismara, E.; Giordano, C. Tetrahedron 1985, 41, 4157-4170. (h) Crabtree, R. H. Pure Appl. Chem. 1995, 67, 39-45. (i) Brown, S. H.; Crabtree, R. H. J. Am. Chem. Soc. 1989, 111, 2935-2946. Reviews containing a brief discussion on this topic include: (j) Walling, C.; Huyser, E. S. Org. React. 1963, 13, 91-149. (k) Abell, P. I. In Free Radicals; Kochi, J. K.,Ed.; Wiley-Interscience: New York, 1973; Vol. 2, p 63. (l) Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds; Pergamon Press: Oxford, UK, 1986.
38. Pioneering studies in this area include: (a) Jacobs, R. L.; Ecke, G. G. J. Org. Chem. 1963, 28, 3036-3038. (b) Dieckmann, J.; Pedersen, C. J. J. Chem. 1964, 29, 2031-2032. (c) Rosenthal, I.; Elad, D. Tetrahedron 1967, 23, 3193-3204. (d) Muramatsu, H.; Inukai, K.; Ueda, T. J. Org. Chem. 1964, 29, 2220-2223. (e) Citterio, A.; Arnoldi, A.; Griffini, A. Tetrahedron 1982, 38, 393-395. (f) Matthews, D. P.; McCarthy, J. R. J. Org. Chem. 1990, 55, 2973-2975. (g) Minisci, F.; Citterio, A.; Vismara, E.; Giordano, C. Tetrahedron 1985, 41, 4157-4170. (h) Crabtree, R. H. Pure Appl. Chem. 1995, 67, 39-45. (i) Brown, S. H.; Crabtree, R. H. J. Am. Chem. Soc. 1989, 111, 2935-2946. Reviews containing a brief discussion on this topic include: (j) Walling, C.; Huyser, E. S. Org. React. 1963, 13, 91-149. (k) Abell, P. I. In Free Radicals; Kochi, J. K.,Ed.; Wiley-Interscience: New York, 1973; Vol. 2, p 63. (l) Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds; Pergamon Press: Oxford, UK, 1986.
39. Pioneering studies in this area include: (a) Jacobs, R. L.; Ecke, G. G. J. Org. Chem. 1963, 28, 3036-3038. (b) Dieckmann, J.; Pedersen, C. J. J. Chem. 1964, 29, 2031-2032. (c) Rosenthal, I.; Elad, D. Tetrahedron 1967, 23, 3193-3204. (d) Muramatsu, H.; Inukai, K.; Ueda, T. J. Org. Chem. 1964, 29, 2220-2223. (e) Citterio, A.; Arnoldi, A.; Griffini, A. Tetrahedron 1982, 38, 393-395. (f) Matthews, D. P.; McCarthy, J. R. J. Org. Chem. 1990, 55, 2973-2975. (g) Minisci, F.; Citterio, A.; Vismara, E.; Giordano, C. Tetrahedron 1985, 41, 4157-4170. (h) Crabtree, R. H. Pure Appl. Chem. 1995, 67, 39-45. (i) Brown, S. H.; Crabtree, R. H. J. Am. Chem. Soc. 1989, 111, 2935-2946. Reviews containing a brief discussion on this topic include: (j) Walling, C.; Huyser, E. S. Org. React. 1963, 13, 91-149. (k) Abell, P. I. In Free Radicals; Kochi, J. K.,Ed.; Wiley-Interscience: New York, 1973; Vol. 2, p 63. (l) Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds; Pergamon Press: Oxford, UK, 1986.
40. Pioneering studies in this area include: (a) Jacobs, R. L.; Ecke, G. G. J. Org. Chem. 1963, 28, 3036-3038. (b) Dieckmann, J.; Pedersen, C. J. J. Chem. 1964, 29, 2031-2032. (c) Rosenthal, I.; Elad, D. Tetrahedron 1967, 23, 3193-3204. (d) Muramatsu, H.; Inukai, K.; Ueda, T. J. Org. Chem. 1964, 29, 2220-2223. (e) Citterio, A.; Arnoldi, A.; Griffini, A. Tetrahedron 1982, 38, 393-395. (f) Matthews, D. P.; McCarthy, J. R. J. Org. Chem. 1990, 55, 2973-2975. (g) Minisci, F.; Citterio, A.; Vismara, E.; Giordano, C. Tetrahedron 1985, 41, 4157-4170. (h) Crabtree, R. H. Pure Appl. Chem. 1995, 67, 39-45. (i) Brown, S. H.; Crabtree, R. H. J. Am. Chem. Soc. 1989, 111, 2935-2946. Reviews containing a brief discussion on this topic include: (j) Walling, C.; Huyser, E. S. Org. React. 1963, 13, 91-149. (k) Abell, P. I. In Free Radicals; Kochi, J. K.,Ed.; Wiley-Interscience: New York, 1973; Vol. 2, p 63. (l) Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds; Pergamon Press: Oxford, UK, 1986.
41. Pioneering studies in this area include: (a) Jacobs, R. L.; Ecke, G. G. J. Org. Chem. 1963, 28, 3036-3038. (b) Dieckmann, J.; Pedersen, C. J. J. Chem. 1964, 29, 2031-2032. (c) Rosenthal, I.; Elad, D. Tetrahedron 1967, 23, 3193-3204. (d) Muramatsu, H.; Inukai, K.; Ueda, T. J. Org. Chem. 1964, 29, 2220-2223. (e) Citterio, A.; Arnoldi, A.; Griffini, A. Tetrahedron 1982, 38, 393-395. (f) Matthews, D. P.; McCarthy, J. R. J. Org. Chem. 1990, 55, 2973-2975. (g) Minisci, F.; Citterio, A.; Vismara, E.; Giordano, C. Tetrahedron 1985, 41, 4157-4170. (h) Crabtree, R. H. Pure Appl. Chem. 1995, 67, 39-45. (i) Brown, S. H.; Crabtree, R. H. J. Am. Chem. Soc. 1989, 111, 2935-2946. Reviews containing a brief discussion on this topic include: (j) Walling, C.; Huyser, E. S. Org. React. 1963, 13, 91-149. (k) Abell, P. I. In Free Radicals; Kochi, J. K.,Ed.; Wiley-Interscience: New York, 1973; Vol. 2, p 63. (l) Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds; Pergamon Press: Oxford, UK, 1986.
42. Pioneering studies in this area include: (a) Jacobs, R. L.; Ecke, G. G. J. Org. Chem. 1963, 28, 3036-3038. (b) Dieckmann, J.; Pedersen, C. J. J. Chem. 1964, 29, 2031-2032. (c) Rosenthal, I.; Elad, D. Tetrahedron 1967, 23, 3193-3204. (d) Muramatsu, H.; Inukai, K.; Ueda, T. J. Org. Chem. 1964, 29, 2220-2223. (e) Citterio, A.; Arnoldi, A.; Griffini, A. Tetrahedron 1982, 38, 393-395. (f) Matthews, D. P.; McCarthy, J. R. J. Org. Chem. 1990, 55, 2973-2975. (g) Minisci, F.; Citterio, A.; Vismara, E.; Giordano, C. Tetrahedron 1985, 41, 4157-4170. (h) Crabtree, R. H. Pure Appl. Chem. 1995, 67, 39-45. (i) Brown, S. H.; Crabtree, R. H. J. Am. Chem. Soc. 1989, 111, 2935-2946. Reviews containing a brief discussion on this topic include: (j) Walling, C.; Huyser, E. S. Org. React. 1963, 13, 91-149. (k) Abell, P. I. In Free Radicals; Kochi, J. K.,Ed.; Wiley-Interscience: New York, 1973; Vol. 2, p 63. (l) Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds; Pergamon Press: Oxford, UK, 1986.
43. (a) Gong, J.; Fuchs, P. L. J. Am. Chem. Soc. 1996, 118, 4486-4487.
44. (b) Xiang, J.; Fuchs, P. L. J. Am. Chem. Soc. 1996, 118, 11986-11987.
45. (c) Xiang, J.; Jiang, W.; Gong, J.; Fuchs, P. L. J. Am. Chem. Soc. 1997, 119, 4123-4129 and references therein.
46. (a) Yamada, K.; Fujihara, H.; Yamamoto, Y.; Miwa, Y.; Taga, Y.; Tomioka, K. Org. Lett. 2002, 4, 3509-3511.
47. (b) Yamada, K.; Yamamoto, Y.; Tomioka, K. Org. Lett. 2003, 5, 1797-1799.
48. (c) Yamamoto, Y.; Yamada, K.; Tomioka, K. Tetrahedron Lett. 2004, 45, 795-797.
49. (d) Yamada, K.; Yamamoto, Y.; Maekawa, M.; Tomioka, K. J. Org. Chem. 2004, 69, 1531-1534.
50. (e) Yamamoto, Y.; Maekawa, M.; Akindele, T.; Yamada, K.; Tomioka, K. Tetrahedron 2005, 61, 379-384.
51. (f) Yamada, K.; Yamamoto, Y.; Tomioka, K. J. Synth. Org. Chem., Jpn. 2004, 62, 1158-1165.
52. Hirao, K.; Sakaguchi, S.; Ishii, Y. Tetrahedron Lett. 2002, 43, 3617-3620.
53. Kim, S.; Kim, N.; Chung, W.-J.; Cho, C. H. Synlett 2001, 937-940.
54. (a) Fernandez, M.; Alonso, R. Org. Lett. 2003, 5, 2461-2464.
55. (b) Torrente, S.; Alonso, R. Org. Lett. 2001, 3, 1985-1987.
56. Yoshimitsu, T.; Tsunoda, M.; Nagaoka, H. Chem. Commun. 1999, 1745-1746.
57. Recent reviews of triethylborane chemistry include: (a) Ollivier, C.; Renaud, P. Chem Rev. 2001, 101, 3415-3434. (b) Yorimitsu, H.; Oshima, K. In Radicals in Organic Synthesis; Renaud, P., Sibi, M. P., Eds.: Wiley-VCH: Weinheim, Germany, 2001; Vol. 1, pp 11-27. (c) O'Mahony, G. Synlett 2004, 572-573.
58. Recent reviews of triethylborane chemistry include: (a) Ollivier, C.; Renaud, P. Chem Rev. 2001, 101, 3415-3434. (b) Yorimitsu, H.; Oshima, K. In Radicals in Organic Synthesis; Renaud, P., Sibi, M. P., Eds.: Wiley-VCH: Weinheim, Germany, 2001; Vol. 1, pp 11-27. (c) O'Mahony, G. Synlett 2004, 572-573.
59. Recent reviews of triethylborane chemistry include: (a) Ollivier, C.; Renaud, P. Chem Rev. 2001, 101, 3415-3434. (b) Yorimitsu, H.; Oshima, K. In Radicals in Organic Synthesis; Renaud, P., Sibi, M. P., Eds.: Wiley-VCH: Weinheim, Germany, 2001; Vol. 1, pp 11-27. (c) O'Mahony, G. Synlett 2004, 572-573.
60. Yoshimitsu, T.; Arano, Y.; Nagaoka, H. J. Org. Chem. 2003, 68, 625-627.
61. Yoshimitsu, T.; Makino, T.; Nagaoka, H. J. Org. Chem. 2003, 68, 7548-7550.
62. Yoshimitsu, T.; Makino, T.; Nagaoka, H. J. Org. Chem. 2004, 69, 1993-1998.
63. 4e,f
64. Comprehensive reviews of the addition of carbon-centered radicals to alkenes: (a) Fischer, H.; Radom, L. Angew. Chem., Int. Ed. 2001, 40, 1340-1371. (b) Giese, B. Angew. Chem., Int. Ed. Engl. 1983, 22, 753-764. (c) Reference 4h. (d) Curran, D. P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Semmelhack, M. F., Eds.: Pergamon: Oxford, UK, 1991; Vol. 4.
65. Comprehensive reviews of the addition of carbon-centered radicals to alkenes: (a) Fischer, H.; Radom, L. Angew. Chem., Int. Ed. 2001, 40, 1340-1371. (b) Giese, B. Angew. Chem., Int. Ed. Engl. 1983, 22, 753-764. (c) Reference 4h. (d) Curran, D. P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Semmelhack, M. F., Eds.: Pergamon: Oxford, UK, 1991; Vol. 4.
66. Comprehensive reviews of the addition of carbon-centered radicals to alkenes: (a) Fischer, H.; Radom, L. Angew. Chem., Int. Ed. 2001, 40, 1340-1371. (b) Giese, B. Angew. Chem., Int. Ed. Engl. 1983, 22, 753-764. (c) Reference 4h. (d) Curran, D. P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Semmelhack, M. F., Eds.: Pergamon: Oxford, UK, 1991; Vol. 4.
67. Comprehensive reviews of the addition of carbon-centered radicals to alkenes: (a) Fischer, H.; Radom, L. Angew. Chem., Int. Ed. 2001, 40, 1340-1371. (b) Giese, B. Angew. Chem., Int. Ed. Engl. 1983, 22, 753-764. (c) Reference 4h. (d) Curran, D. P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Semmelhack, M. F., Eds.: Pergamon: Oxford, UK, 1991; Vol. 4.
68. Zytowski, T.; Fischer, H. J. Am. Chem. Soc. 1986, 118, 437-439.
69. 3B/air system: Sato, T.; Hibino, K.; Otsu, T. Nippon Kagakukai Shi 1975, 1080-1084. Also, see: Chung, T. C.; Janvikul, W.; Lu, H. L. J. Am. Chem. Soc. 1996, 118, 705-706.
70. 3B/air system: Sato, T.; Hibino, K.; Otsu, T. Nippon Kagakukai Shi 1975, 1080-1084. Also, see: Chung, T. C.; Janvikul, W.; Lu, H. L. J. Am. Chem. Soc. 1996, 118, 705-706.
71. Possible precoordination of triethylborane with carbonyl compounds, see: Beraud, V.; Gnanou, Y.; Walton, J. C.; Maillard, B. Tetrahedron Lett. 2000, 41, 1195-1198.