A new stereocontrolled approach to 1β-methylcarbapenem: Asymmetric hydroformylation of 4-vinyl β-lactams catalyzed by Rh(I) complexes of chiral phosphine - phosphites and phosphine - phosphinites

Journal of Organic Chemistry

Volumn 61, Issue 22, 1996, Pages 7658-7659

  Nozaki, Kyoko ^a   Li, Wen Ge ^a   Horiuchi, Toshihide ^a   Takaya, Hidemasa ^a   Saito, Takao ^b   Yoshida, Akifumi ^b   Matsumura, Kazuhiko ^b   Kato, Yasushi ^b   Imai, Takashi ^b   Miura, Takashi ^b   Kumobayashi, Hidenori ^b  

^a KYOTO UNIVERSITY   (Japan)

^b TAKASAGO INTERNATIONAL CORPORATION   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1BETA METHYLCARBAPENEM; CARBAPENEM DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY; TECHNIQUE;

EID: 0029825118     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961689m     Document Type: Article

References (16)

1. (a) Shih, D. H.; Baker, F.; Cama, L. D.; Christensen, B. G. Heterocydes 1984, 21, 29.
2. (b) Shih, D. H.; Cama, L. D.; Christensen, B. G. Tetrahedron Lett. 1985, 26, 587.
3. Recent references for this approach: (a) Shirai, F.; Nakai, T. J. Org. Chem. 1987, 52, 5491 and references cited therein. (b) Nagao, Y.; Nagase, Y.; Kumagai, T.; Matsunage, H.; Abe, T.; Shimada, O.; Hayashi, T.; Inoue, Y. J. Org. Chem. 1992, 57, 4243 and references cited therein.
4. Recent references for this approach: (a) Shirai, F.; Nakai, T. J. Org. Chem. 1987, 52, 5491 and references cited therein. (b) Nagao, Y.; Nagase, Y.; Kumagai, T.; Matsunage, H.; Abe, T.; Shimada, O.; Hayashi, T.; Inoue, Y. J. Org. Chem. 1992, 57, 4243 and references cited therein.
5. Other recent approaches: Tsukada, N.; Shimada, T.; Gyoung, Y. S.; Asao, N.; Yamamoto, Y. J. Org. Chem. 1995, 60, 143 and references cited therein.
6. (a) Sakai, N.; Mano, S.; Nozaki, K.; Takaya, H. J. Am. Chem. Soc. 1993, 115, 7033.
7. (b) Sakai, N.; Nozaki, K.; Takaya, H. J. Chem. Soc., Chem. Commun. 1994, 395.
8. Higashizima, T.; Sakai, N.; Nozaki, K.; Takaya, H. Tetrahedron Lett. 1994, 35, 2023.
9. Nanno, T.; Sakai, N.; Nozaki, K.; Takaya, H. Tetrahedron: Asymmetry 1995, 6, 2583.
10. (e) Horiuchi, T.; Ohta, T.; Nozaki, K.; Takaya, H. Chem. Commun. 1996, 155.
11. The 4-vinyl-β-lactam 3 was prepared from 4-acetoxy-2-azetidinone 2 by addition of vinyl Grignard reagent. Kobayashi, T.; Ishida, N.; Hiraoka, T. J. Chem. Soc., Chem. Commun. 1980, 736.
12. We previously reported the synthesis of 2 using asymmetric hydrogenation as a key step. Mashima, K.; Kusano, K.; Sato, N.; Matsumura, Y.; Nozaki, K.; Kumobayashi, H.; Sayo, N.; Hori, Y.; Ishizaki, T.; Akutagawa, S.; Takaya, H. J. Org. Chem. 1994, 59, 3064.
13. Sakai, N. Highly stereoselective organic synthesis by use of transition-metal catalyzed reactions of carbon monoxide and olefins, Kyoto University, 1994.
14. Detailed results on hydroformylation of 6 are given in the supporting information.
15. Merkin, P.; Muetterties, E. L.; Jesson, J. P. J. Am. Chem. Soc. 1972, 94, 5271.
16. P-Rh = 40.0 Hz, for phosphinite).