Intramolecular Radical Cyclization of 2-Haloethanal Allyl Acetal and Allyl 2-Halophenyl Ether with a Grignard Reagent in the Presence of Iron(II) Chloride

Author:

Hayashi Yasuhiro,Shinokubo Hiroshi,Oshima Koichiro

Publisher

Elsevier BV

Subject

Organic Chemistry,Drug Discovery,Biochemistry

Reference11 articles.

1. a) Giese, B. “Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds,” ed by Baldwin, J.E. Pergamon Press, Oxford (1986). b) Giese, B. Angew. Chem. Int. Ed. Engl., 1989, 28, 969–980. c) Curran, D.P.; Shen, W.; Zhang, J.; Heffner, T.A. J. Am. Chem. Soc., 1990, 112, 6738–6740. d) Porter, N.A.; Scott, D.M.; Rosenstein, I.J.; Giese, B.; Veit, A.; Zeitz, H.G. J. Am. Chem. Soc., 1991, 113, 1791–1799. Curran, D.P. in “Comprehensive Organic Synthesis,” ed by Trost, B.M.; Fleming, I. Pergamon Press, Oxford (1991), Vol. 4, Chap. 4.2, p. 779–831.

2. Nakao, J.; Inoue, R.; Shinokubo, H. Oshima, K. J. Org. Chem., 1997, 62, 1910–1911. Inoue, R.; Nakao, J.; Shinokubo, H. Oshima, K. Bull. Chem. Soc. Jpn. 1997, 70, 2039–2049.

3. Radical cyclization-trapping in the synthesis of natural products. A simple, stereocontrolled route to prostaglandin F2.alpha.

4. The reaction of 1a with i-PrMgBr provided a mixture of 2a and 3a in almost the same ratio as that with n-BuMgBr.

5. Grieco, P.A.; Oguri, T.; Yokoyama, Y. Tetrahedron Lett., 1978, 419–420. Morikawa, T.; Nishiwaki, T.; Iitake, Y.; Kobayashi, Y. Tetrahedron Lett., 1987, 28, 671–674.

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