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Am. Chem. SOC. 107, 8256 (1985); Tetrahedron Lett. 27, 1441 (1986). [4] Y. Tamura, H. Kondo, H. Annoura, R. Takeuchi, and F. Fujioka, Tetrahedron Lett. 27, 81, 2117 (1986); M. P. Heitz, F. Gellibert, and C. Mioskowski, Tetrahedron Lett. 27, 3859 (1986). [5] M. Suzuki, Y. Kimura. and S. Terashima, Bull. Chem. Jap. 59, 3559 (1986) and ref. cited. [6] G. Castaldi, S. Cavicchioli, C. Giordano, and F. Uggeri, Angew. Chem. 98, 273, Int. Ed. Engl. 25, 259 (1986); G. Castaldi and C. Giordano, Synthesis 1987, 1039.

Hoffmann and S. Froech, Tetrahedron Lett. 26, 1643 (1985). [lo] R. W. Hoffmann, W. Ladner, K. Steinbach, W. Massa, R. Schmidt, and G. Snatzke, Chem. Ber. 114, 2786 (1981). [l 11 R. Hoffmann and T. Herold, Chem. Ber. 114, 375 (1981). [12] R. W. Roush, A. E. Walts, and L. K. Hoong, J. Am. Chem. 107, 8186 (1985). 39 [13] N. Ikeda, I. Arai, and H. Yamamoto, J. Am. Chem. 108, 483 (1986); cf. also: N . Zkeda, K. Omori, and H. Yamamoto,Tetrahedron Lett. 27, 1175 (1986). [14] S. Masamune, W. Choy, J. S.

This is subsequently treated with the titanium reagent (28), which adds in a chemoselective manner exclusively to the aldehyde group (the keto function is not attacked). 5) 3 (29) 90% The ability of the nitro group to stabilize a carbanion can be exploited in the synthesis of macrocyclic lactones and lactams, a process that involves an elegant ring-expansion reac6070 (30) 90% During the reductive amination of ketoaldehyde (31), the ring-expanded product (32) forms spontaneously in 41 % yield [13].

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