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2005
C-C bond formation
O 0282
Sequential Ring-Closing Metathesis/Pd-Catalyzed, Si-Assisted Cross-Coupling
General Synthesis of Highly Substituted Unsaturated Alcohols and
05- 049 Reactions:
Medium-Sized Rings Containing a 1,3-cis—cis Diene Unit. — Olefinic vinyl silyl
ethers undergo molybdenum-catalyzed ring-closing metathesis reactions to give 5-, 6-,
and 7-membered cycloalkenylsiloxanes, which are further act as coupling partners in
palladium-catalyzed inter- or intramolecular cross-coupling reactions with aryl or alkenyl halides. The resulting products, either diaryl-substituted alkenyl alcohols or 8- to
12-membered carbocyclic dienes, are formed in good yields and with high selectivities.
The method can be also extended to the synthesis of oxygen-containing cyclic dienes.
— (DENMARK*, S. E.; YANG, S.-M.; Tetrahedron 60 (2004) 43, 9695-9708; Dep.
Chem., Univ. Ill., Urbana, IL 61801, USA; Eng.) — Klein
2005
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