Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 20, Issue 41, Pages 13117-13121Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201404159
Keywords
aryldiazonium salts; chiral N,N ligand; desymmetrization; Heck reaction; palladium
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Funding
- Sao Paulo Research Foundation - Fapesp [2011/23832-6, 2013/07600-3]
- Fundacao de Amparo a Pesquisa do Estado de Sao Paulo (FAPESP) [11/23832-6, 13/07600-3] Funding Source: FAPESP
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A new enantioselective Heck-Matsuda desymmetrization reaction was accomplished by using 3-cyclopentenol to produce chiral five-membered 4-aryl cyclopentenol scaffolds in good yields and high cc's, together with some 3-aryl-cyclopentanones as minor products. Mechanistically, the hydroxyl group of 3-cyclopentenol acts as a directing group and is responsible for the cis-arrangement in the formation of the 4-aryl-cyclopentenols.
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