By Lutz F. Tietze, Hubertus P. Bell, Gordon Brasche

ISBN-10: 3527290605

ISBN-13: 9783527290604

Domino reactions make it easier to construct complicated buildings in one-pot reactions with no the necessity to isolate intermediates—a dream comes actual. during this publication, the well-respected professional, Professor Lutz Tietze, summarizes the probabilities of this response type—an method for an efficiant, economically benificial and ecological benign synthesis.
A sure needs to for each natural chemist.

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1 Cationic/Cationic Processes AcO H H AcO O O O OAc HO 60% 1-33 1-32 O O O HO 65% AcO OAc AcO 1-35 1-34 O tBuO O O H H O O 60% O O OAc O 1-37 1-36 O O tBuO O O 75% O OAc O O O 1-38 1-39 Reaction conditions: 1 eq BF3•OEt2, CH2Cl2, –40 °C, 10–30 min, H2O quench; then Ac2O, Et2N, CH2Cl2. 10. Synthesis of oxepanes. spectively. 1. 11) [11]. 12). The conformation 1-45, which would lead to 1-46 seems to be disfavored. The tetrahydropyran moiety, another oxacycle, is also found in many biologically active natural products from marine and terrestrial origin.

12 For excellent reviews, see: (a) T. L. B. Boivin, Tetrahedron 1987, 43, 3309−3362; (b) M. C. Elliott, J. Chem. Soc. Perkin Trans. 1 2000, 1291−1318. 13 I. E. -M. Plancher, Tetrahedron Lett. 1999, 40, 5259−5262. 14 B. Leroy, I. E. Markó, J. Org. Chem. 2002, 67, 8744−8752. -P. -C. -Y. Yang, Synthesis 2002, 7, 937−940. -P. -Y. -T. Ma, J. Am. Chem. Soc. P. -T. -Y. Hu, Int. Ed. Engl. Angew. Chem. 2001, 40, 2921−2922. 17 For a excellent review, see: H. N. C. -Y. -W. -C. Yip, J. Tanko, T. Hudlicky, Chem.

Johnson, L. E. Overman, Tetrahedron Lett. 1991, 32, 7361−7364. 6 L. E. Overman, J. P. Wolfe, J. Org. Chem. 2002, 67, 6421−6429. 7 (a) J. K. -H. Hui, J. L. McLaughlin, J. Nat. Prod. 1990, 53, 237− 278; (b) U. Koert, Tetrahedron Lett. 1994, 35, 2517−2520; (c) T. R. Hoye, P. R. Hanson, Tetrahedron Lett. -C. Harmange, B. Figadere, Tetrahedron Lett. 1993, 34, 8093−8096. 8 (a) U. Koert, M. Stein, K. Harms, Tetrahedron Lett. 1993, 34, 2299−2302; (b) U. Koert, H. Wagner, U. Pidun, Chem. Ber. 1994, 127, 1447−1457.

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Domino Reactions in Organic Synthesis by Lutz F. Tietze, Hubertus P. Bell, Gordon Brasche


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