A one-pot primary aminomethylation of aryl halides, triflates, mesylates, and tosylates via Suzuki-Miyaura cross-coupling reactions with sodium phthalimidomethyltrifluoroborate followed by deamidation with ethylenediamine is reported.

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[reaction: see text] The highly stereoselective construction of the C3 stereogenic center of the taxol C-ring is described. The trans isomer at the C3-C8 position of the taxol C-ring, which is required for the total synthesis, as well as its diastereomeric cis isomer were successfully synthesized with highly diastereoselective S(N)2' reduction of the allylic phosphonium salts.

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Construction of eight-membered carbocyclic rings via the intramolecular B-alkyl Suzuki-Miyaura cross-coupling reaction has been studied. This protocol proved its potency through the formation of the eight-membered ring possessing a quaternary carbon on its ring in high yield, affording promise of a new access to the eight-membered ring of Taxol. [reaction: see text]

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Reaction. -(KAWADA, H.; IWAMOTO, M.; UTSUGI, M.; MIYANO, M.; NAKADA*, M.; Org. Lett. 6 (2004) 24, 4491-4494; Dep. Chem., Sch. Sci. Eng., Waseda Univ., Shinjuku, Tokyo 169, Japan; Eng.) -Lindner 12-192