Ru-catalyzed hydrogenolysis of chiral allylic and propargylic cyclic carbonates: Synthesis of optically active (E)-allylic and allenic alcohols

Synthetic Communications

Volumn 26, Issue 8, 1996, Pages 1485-1492

  Kang, Suk Ku ^a   Kim, Dae Yeun ^a   Rho, Ho Sik ^a   Yoon, Seung Hyun ^a   Ho, Pil Su ^a  

^a Sungkyunkwan University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; ALLYL ALCOHOL; ALLYL COMPOUND;

ARTICLE; CATALYSIS; CHIRALITY; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029978083     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919608003514     Document Type: Article

References (18)

1. Preparation of optically active allenic alcohols: (a) Cowie, J. S.; Landor, P. D.; Landor, S. R. J. Chem. Soc. Perkin Trans. I 1973, 720. (b) Alexakis, A.; Marek, I.; Mangeney, P.; Normant, J. F. Tetrahedron 1991, 47, 1677. (c) Oehlschager, A. C.; Czyewska, E. Tetraheron Lett. 1983, 24, 5587. (d) Kang, S-K.; Kim, S-G.; Cho, D-G. Tetrahedron:Asymmetry 1992, 3, 1509.
2. Preparation of optically active allenic alcohols: (a) Cowie, J. S.; Landor, P. D.; Landor, S. R. J. Chem. Soc. Perkin Trans. I 1973, 720. (b) Alexakis, A.; Marek, I.; Mangeney, P.; Normant, J. F. Tetrahedron 1991, 47, 1677. (c) Oehlschager, A. C.; Czyewska, E. Tetraheron Lett. 1983, 24, 5587. (d) Kang, S-K.; Kim, S-G.; Cho, D-G. Tetrahedron:Asymmetry 1992, 3, 1509.
3. Preparation of optically active allenic alcohols: (a) Cowie, J. S.; Landor, P. D.; Landor, S. R. J. Chem. Soc. Perkin Trans. I 1973, 720. (b) Alexakis, A.; Marek, I.; Mangeney, P.; Normant, J. F. Tetrahedron 1991, 47, 1677. (c) Oehlschager, A. C.; Czyewska, E. Tetraheron Lett. 1983, 24, 5587. (d) Kang, S-K.; Kim, S-G.; Cho, D-G. Tetrahedron:Asymmetry 1992, 3, 1509.
4. Preparation of optically active allenic alcohols: (a) Cowie, J. S.; Landor, P. D.; Landor, S. R. J. Chem. Soc. Perkin Trans. I 1973, 720. (b) Alexakis, A.; Marek, I.; Mangeney, P.; Normant, J. F. Tetrahedron 1991, 47, 1677. (c) Oehlschager, A. C.; Czyewska, E. Tetraheron Lett. 1983, 24, 5587. (d) Kang, S-K.; Kim, S-G.; Cho, D-G. Tetrahedron:Asymmetry 1992, 3, 1509.
5. Gao, Y.; Hanson, R. M.; Klunder, J.; Ko, S. Y.; Masamune, H.; Sharpless, K. B. J. Am. Chem. Soc. 1987, 109, 5765.
6. Corey, E. J.; Yu, C-M.; Lee D-H. J. Am. Chem. Soc. 1990, 112, 878.
7. Kang, S-K.; Park, D-C.; Cho, D-G.; Rho, H-S.; Yu, C-M.; Hong, J-H. Synth. Commun. 1995, 25, 203.
8. Kang, S-K.; Park, D-C.; Cho, D-G.; Chung, J-U.; Jung, K-Y. J. Chem. Soc. Perkin Trans. I 1994, 237.
9. Palladium-catalyzed reduction C-O bond cleavage of allylic esters and carbonates to give terminal olefins with ammonium formate: (a) Tsuji, J.; Yamakawa, T. Tetraheron Lett. 1979, 613. (b) Tsuji, J.; Shimizu, I.; Minami, I. Chem. Lett. 1984, 1017. (c) Tsuji, J. Minami, I.; Shimizu, I. Synthesis 1986, 623. Mandai, T.; Matsumoto, T.; Kawada, M.; Tsuji, J. J. Org. Chem. 1992, 57, 1326. (e) Mandai, T. ; Matsumoto, T.; Kawada, M.; Tsuji, J. ibid. 1992, 57, 6090. (f) Tsuji, J.; Sigiura, T.; Yuhara, M.; Minami, I. J. Chem. Soc. Chem. Commun. 1986, 922. (g) Mandai, T.; Matsumoto, T.; Kawada, M.; Tsuji, J. Tetraheron Lett. 1993, 34, 2160.
10. Palladium-catalyzed reduction C-O bond cleavage of allylic esters and carbonates to give terminal olefins with ammonium formate: (a) Tsuji, J.; Yamakawa, T. Tetraheron Lett. 1979, 613. (b) Tsuji, J.; Shimizu, I.; Minami, I. Chem. Lett. 1984, 1017. (c) Tsuji, J. Minami, I.; Shimizu, I. Synthesis 1986, 623. Mandai, T.; Matsumoto, T.; Kawada, M.; Tsuji, J. J. Org. Chem. 1992, 57, 1326. (e) Mandai, T. ; Matsumoto, T.; Kawada, M.; Tsuji, J. ibid. 1992, 57, 6090. (f) Tsuji, J.; Sigiura, T.; Yuhara, M.; Minami, I. J. Chem. Soc. Chem. Commun. 1986, 922. (g) Mandai, T.; Matsumoto, T.; Kawada, M.; Tsuji, J. Tetraheron Lett. 1993, 34, 2160.
11. Palladium-catalyzed reduction C-O bond cleavage of allylic esters and carbonates to give terminal olefins with ammonium formate: (a) Tsuji, J.; Yamakawa, T. Tetraheron Lett. 1979, 613. (b) Tsuji, J.; Shimizu, I.; Minami, I. Chem. Lett. 1984, 1017. (c) Tsuji, J. Minami, I.; Shimizu, I. Synthesis 1986, 623. Mandai, T.; Matsumoto, T.; Kawada, M.; Tsuji, J. J. Org. Chem. 1992, 57, 1326. (e) Mandai, T. ; Matsumoto, T.; Kawada, M.; Tsuji, J. ibid. 1992, 57, 6090. (f) Tsuji, J.; Sigiura, T.; Yuhara, M.; Minami, I. J. Chem. Soc. Chem. Commun. 1986, 922. (g) Mandai, T.; Matsumoto, T.; Kawada, M.; Tsuji, J. Tetraheron Lett. 1993, 34, 2160.
12. Palladium-catalyzed reduction C-O bond cleavage of allylic esters and carbonates to give terminal olefins with ammonium formate: (a) Tsuji, J.; Yamakawa, T. Tetraheron Lett. 1979, 613. (b) Tsuji, J.; Shimizu, I.; Minami, I. Chem. Lett. 1984, 1017. (c) Tsuji, J. Minami, I.; Shimizu, I. Synthesis 1986, 623. Mandai, T.; Matsumoto, T.; Kawada, M.; Tsuji, J. J. Org. Chem. 1992, 57, 1326. (e) Mandai, T. ; Matsumoto, T.; Kawada, M.; Tsuji, J. ibid. 1992, 57, 6090. (f) Tsuji, J.; Sigiura, T.; Yuhara, M.; Minami, I. J. Chem. Soc. Chem. Commun. 1986, 922. (g) Mandai, T.; Matsumoto, T.; Kawada, M.; Tsuji, J. Tetraheron Lett. 1993, 34, 2160.
13. Palladium-catalyzed reduction C-O bond cleavage of allylic esters and carbonates to give terminal olefins with ammonium formate: (a) Tsuji, J.; Yamakawa, T. Tetraheron Lett. 1979, 613. (b) Tsuji, J.; Shimizu, I.; Minami, I. Chem. Lett. 1984, 1017. (c) Tsuji, J. Minami, I.; Shimizu, I. Synthesis 1986, 623. Mandai, T.; Matsumoto, T.; Kawada, M.; Tsuji, J. J. Org. Chem. 1992, 57, 1326. (e) Mandai, T. ; Matsumoto, T.; Kawada, M.; Tsuji, J. ibid. 1992, 57, 6090. (f) Tsuji, J.; Sigiura, T.; Yuhara, M.; Minami, I. J. Chem. Soc. Chem. Commun. 1986, 922. (g) Mandai, T.; Matsumoto, T.; Kawada, M.; Tsuji, J. Tetraheron Lett. 1993, 34, 2160.
14. Palladium-catalyzed reduction C-O bond cleavage of allylic esters and carbonates to give terminal olefins with ammonium formate: (a) Tsuji, J.; Yamakawa, T. Tetraheron Lett. 1979, 613. (b) Tsuji, J.; Shimizu, I.; Minami, I. Chem. Lett. 1984, 1017. (c) Tsuji, J. Minami, I.; Shimizu, I. Synthesis 1986, 623. Mandai, T.; Matsumoto, T.; Kawada, M.; Tsuji, J. J. Org. Chem. 1992, 57, 1326. (e) Mandai, T. ; Matsumoto, T.; Kawada, M.; Tsuji, J. ibid. 1992, 57, 6090. (f) Tsuji, J.; Sigiura, T.; Yuhara, M.; Minami, I. J. Chem. Soc. Chem. Commun. 1986, 922. (g) Mandai, T.; Matsumoto, T.; Kawada, M.; Tsuji, J. Tetraheron Lett. 1993, 34, 2160.
15. Palladium-catalyzed reduction C-O bond cleavage of allylic esters and carbonates to give terminal olefins with ammonium formate: (a) Tsuji, J.; Yamakawa, T. Tetraheron Lett. 1979, 613. (b) Tsuji, J.; Shimizu, I.; Minami, I. Chem. Lett. 1984, 1017. (c) Tsuji, J. Minami, I.; Shimizu, I. Synthesis 1986, 623. Mandai, T.; Matsumoto, T.; Kawada, M.; Tsuji, J. J. Org. Chem. 1992, 57, 1326. (e) Mandai, T. ; Matsumoto, T.; Kawada, M.; Tsuji, J. ibid. 1992, 57, 6090. (f) Tsuji, J.; Sigiura, T.; Yuhara, M.; Minami, I. J. Chem. Soc. Chem. Commun. 1986, 922. (g) Mandai, T.; Matsumoto, T.; Kawada, M.; Tsuji, J. Tetraheron Lett. 1993, 34, 2160.
16. Ruthenium-catalyzed reductive cleavage of allylic esters with formic acid and triethylamine to give a mixture of regioisomeric olefins is known. See, Maruyama, Y.; Sezaki, T.; Tekawa, M.; Sakamoto, T.; Shimizu, I.; Yamamoto, A. J. Organomet. Chem. 1994, 473, 257.
17. Johnson, R. A.; Sharpless, K. B. Catalytic Asymmetric Synthesis; Ojima, I. Ed.,VHD: New York 1993; Chap. 4.
18. Kang, S-K., Lee, D-H.; Sim, H-S.; Lim, J-S. Tetraheron Lett. 1993, 34, 91.