A new asymmetric route to synthetically useful γ-substituted γ- butyrolactones

Tetrahedron Letters

Volumn 41, Issue 20, 2000, Pages 4003-4006

  Kiegiel, Jaroslaw ^a   Nowacki, Jacek ^a   Tarnowska, Aldona ^a   Stachurska, Malgorzata ^a   Jurczak, Janusz ^a,b  

^a UNIVERSITY OF WARSAW   (Poland)

^b INSTITUTE OF ORGANIC CHEMISTRY   (Poland)

Author keywords

butyrolactones; Asymmetric hydrogenation; Diethyl 3,4 dioxohexanedioate

Indexed keywords

GAMMA BUTYROLACTONE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; ENANTIOMER; HYDROGENATION; REACTION ANALYSIS; SYNTHESIS;

EID: 0034697466     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00538-4     Document Type: Article

References (21)

1. Hizuka, M.; Hayashi, N.; Kamashita, T.; Suemune, H.; Sakai, K. Chem. Pharm. Bull. 1988, 36, 1550.
2. Tanaka, M.; Murakami, T.; Suemune, H; Sakai, K. Heterocycles 1992, 33, 697.
3. Hizuka, M.; Fang, C.; Suemune, H.; Sakai, K. Chem. Pharm. Bull. 1989, 37, 1185.
4. Herradon, B. Tetrahedron: Asymmetry 1991, 2, 191.
5. (a) Suemune, H.; Hizuka, M.; Kamashita, T.; Sakai, K. Chem. Pharm. Bull. 1989, 37, 1379;
6. (b) Ribbons, D. W.; Sutherland, A. G. Tetrahedron 1994, 50, 3587.
7. (a) Labelle, M.; Guindon, Y. J. Am. Chem. Soc. 1989, 111, 2204;
8. (b) Yokomatsu, T.; Yuasa, Y.; Kano, S.; Shibuya, S. Heterocycles 1991, 32, 2315;
9. (c) Taniguchi, T.; Ogasawara, K. Tetrahedron Lett. 1997, 38, 433.
10. To the best of our knowledge, the only reported method to prepare (+)-(R,R)-dilactone 2 in enantiomerically pure form consists of resolution of racemic 3,4-dihydroxyhexanedioic acid and subsequent cyclization (Posternak, T.; Susz, J.-P. Helv. Chim. Acta 1956, 236, 2033).
11. Noyori, R. In Asymmetric Catalysis in Organic Synthesis. Homogenous asymmetric hydrogenation. John Wiley & Sons, Inc.: New York, 1994; Chapter 2, p. 16 and references cited therein.
12. (a) Shao, L.; Seki, T.; Kawano, H.; Saburi, M. Tetrahedron Lett. 1991, 52, 7699;
13. (b) Shao, L.; Kawano, H.; Saburi, M.; Uchida, Y. Tetrahedron 1993, 49, 1997;
14. (c) Wovkulich, P. M.; Shankaran, K.; Kiegiel, J.; Uskokovic, M. R. J. Org. Chem. 1993, 58, 832;
15. (d) Blandin, V.; Carpentier, J.-F.; Mortreux, A. Tetrahedron: Asymmetry 1998, 9, 2765.
16. Diethyl 3,4-dioxohexanedioate was obtained by Claisen condensation of ethyl acetate with diethyl oxalate in 33% yield (Lipiec, T. Acta Pol. Pharm. 1938, 2, 140).
17. Kitamura, M.; Ohkuma, T.; Inoue, S.; Sayo, N.; Kumobayashi, H.; Akutagawa, S.; Ohta, N.; Takaya, H.; Noyori, R. J. Am. Chem. Soc. 1988, 110, 629.
18. 20 -80.9 (c 0.865, AcOEt)}.
19. (a) Nagao, Y.; Dai, W.-M.; Ochiai, M.; Shiro, S. J. Org. Chem. 1989, 54, 5211;
20. (b) Takahata, H.; Uchida, Y.; Momose, T. Tetrahedron Lett. 1994, 35, 4123;
21. (c) Takahata, H.; Uchida, Y.; Momose, T. J. Org. Chem. 1995, 60, 5628.