Dialkylation of gem-dibromocyclopropanes with trialkylmanganate and manganese(II) chloride-catalyzed reaction with alkylmagnesium bromide

Tetrahedron Letters

Volumn 37, Issue 30, 1996, Pages 5377-5380

  Inoue, Rie ^a   Shinokubo, Hiroshi ^a   Oshima, Koichiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPROPANE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030598030     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01082-9     Document Type: Article

References (14)

1. 1. Kitatani, K.; Hiyama, T.; Nozaki, H. J. Am. Chem. Soc. 1976, 98, 2362-2364; idem Bull. Chem. Soc. Jpn. 1977, 50, 1600-1607; idem Bull. Chem. Soc. Jpn. 1977, 50, 3288-3294; Kitatani, K.; Yamamoto, H.; Hiyama, T.; Nozaki, H. Bull. Chem. Soc. Jpn. 1977, 50, 2158-2160.
2. 1. Kitatani, K.; Hiyama, T.; Nozaki, H. J. Am. Chem. Soc. 1976, 98, 2362-2364; idem Bull. Chem. Soc. Jpn. 1977, 50, 1600-1607; idem Bull. Chem. Soc. Jpn. 1977, 50, 3288-3294; Kitatani, K.; Yamamoto, H.; Hiyama, T.; Nozaki, H. Bull. Chem. Soc. Jpn. 1977, 50, 2158-2160.
3. 1. Kitatani, K.; Hiyama, T.; Nozaki, H. J. Am. Chem. Soc. 1976, 98, 2362-2364; idem Bull. Chem. Soc. Jpn. 1977, 50, 1600-1607; idem Bull. Chem. Soc. Jpn. 1977, 50, 3288-3294; Kitatani, K.; Yamamoto, H.; Hiyama, T.; Nozaki, H. Bull. Chem. Soc. Jpn. 1977, 50, 2158-2160.
4. 1. Kitatani, K.; Hiyama, T.; Nozaki, H. J. Am. Chem. Soc. 1976, 98, 2362-2364; idem Bull. Chem. Soc. Jpn. 1977, 50, 1600-1607; idem Bull. Chem. Soc. Jpn. 1977, 50, 3288-3294; Kitatani, K.; Yamamoto, H.; Hiyama, T.; Nozaki, H. Bull. Chem. Soc. Jpn. 1977, 50, 2158-2160.
5. 2. Harada, T.; Katsuhira, T.; Hattori, K.; Oku, A. J. Org. Chem. 1993. 58, 2958-2965; Harada, T.; Hattori, K.; Katsuhira, T.; Oku, A. Tetrahedron Lett. 1989, 30, 6035-6038, 6039-6040.
6. . 2. Harada, T.; Katsuhira, T.; Hattori, K.; Oku, A. J. Org. Chem. 1993. 58, 2958-2965; Harada, T.; Hattori, K.; Katsuhira, T.; Oku, A. Tetrahedron Lett. 1989, 30, 6035-6038, 6039-6040.
7. 3. Cyclopropylborate has been also reported to undergo similar 1,2-migration: Danheiser, R. L.; Savoca, A. C. J. Org. Chem. 1985, 50, 2401-2403.
8. +) have been reported. Normant, J. F.; Cahiez, G. "Organomanganous Reagents" in Modern Synthetic Methods, Vol. 3, pp. 173-216, 1983, Scheffold, R. Ed., Otto Salle Verlag GmbH & Co., Frankfurt am Main.
9. 5. Fugami, K.; Hibino, J.; Nakatsukasa, S.; Matsubara, S.; Oshima, K.; Utimoto, K.; Nozaki, H. Tetrahedron 1988, 44, 4277-4292. Fugami, K.; Oshima, K.; Utimoto, K.; Nozaki, H. Tetrahedron Lett. 1986, 27, 2161-2164.
10. 5. Fugami, K.; Hibino, J.; Nakatsukasa, S.; Matsubara, S.; Oshima, K.; Utimoto, K.; Nozaki, H. Tetrahedron 1988, 44, 4277-4292. Fugami, K.; Oshima, K.; Utimoto, K.; Nozaki, H. Tetrahedron Lett. 1986, 27, 2161-2164.
11. 25I: C, 50.66; H, 8.17%.
12. 2O before being converted to 5.
13. 8. Cahiez, G.; Laboue, B. Tetrahedron Lett. 1989, 30, 7369-7372 and references cited therein.
14. 9. 1-Alkylcyclopropylzincates have been reported to react with alkenyl halide in the presence of a Pd catalyst. See ref 2.