cis-Oxypalladation complexes derived from (1R,5R)-2(10),3-pinadiene and their utilization in Pd(II)-catalyzed enantioselective cyclization of 2-(trans-2-butenyl)phenols.
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概要
- 論文の詳細を見る
(1<I>R</I>,5<I>R</I>)-2(10),3-Pinadiene, when treated with either Na<SUB>2</SUB>PdCl<SUB>4</SUB> in MeOH or Pd(OAc)<SUB>2</SUB> in AcOH and NaCl, gives di-μ-chloro-bis[(3,2,10-η-<I>cis</I>-4-methoxy or acetoxypinene)palladium(II)] (<B>4a</B>) or (<B>4b</B>), respectively. These complexes represent the firstly isolated <I>cis</I>-oxypalladation adduct. The ligand exchange of <B>4b</B> with AgOAc affords di-μ-acetato-bis[(3,2,10-η-<I>cis</I>-4-acetoxypinene)palladium(II)] (<B>5b</B>) which serves as the catalyst for the asymmetric cyclization of 2-(<I>trans</I>-2-butenyl)phenols leading to 2-vinyl-2,3-dihydrobenzofurans (<B>13</B>). Although the enantioselectivities induced in this asymmetric cyclization are not high (1–29% ee), noteworthy is that the <I>cis</I>-complex <B>5b</B> affords (<I>R</I>)-(−)-enantiomer of <B>13</B> while the parent di-μ-acetato-bis[(3,2,10-η-pinene)palladium(II)] give the (<I>S</I>)-isomer. As an application of the present asymmetric cyclization, attempts to synthesize (<I>S</I>)-(+)-tremetone have been made.
- 公益社団法人 日本化学会の論文
著者
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Hosokawa Takahiro
Department Of Biology Faculty Of Science Kobe University
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Imada Yasushi
Department Of Chemical Engineering Osaka Prefecture University
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Murahashi Shun-ichi
Department Of Applied Chemistry Okayama University Of Science
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