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Oxirane derivativesR 0030 Synthesis of Epoxides by Palladium-Catalyzed Reactions of Tertiary Allyl Alco-
hols with Aryl or Alkenyl Halides. — In the new palladium-catalyzed synthesis, both the C—O bond of the epoxide and a C—C bond to an aryl halide are constructed in a single operation. Only several biaryl phosphines (I)-(III) and Xantphos are suitable lig-ands; the Mizoroki—Heck reaction of tertiary alcohols with aryl halides predominates when other phosphines are used. The diastereoselectivities in the case of substrates with a stereogenic center such as (XVIII) or (XXI) depend strongly on the bulkiness of the substituents. — (HAYASHI, S.; YORIMITSU*, H.; OSHIMA, K.; J. Am. Chem. Soc. 131 (2009) 6, 2052-2053; Dep. Mater. Chem., Grad. Sch. Eng., Kyoto Univ., Nishikyo, Kyoto 615, Japan; Eng.) — Kieslich
27- 088
ChemInform 2009, 40, issue 01 © 2009 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
www.cheminform.wiley-vch.de
ChemInform 2009, 40, issue 01 © 2009 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim