A General and Regioselective Synthesis of Cyclopentenone Derivatives through Nickel(0)-Mediated [3 + 2] Cyclization of Alkenyl Fischer Carbene Complexes and Internal Alkynes
详细信息 查看全文
- 作者：José ; Barluenga ; Pablo Barrio ; Lorena Riesgo ; Luis. A. Ló ; pez ; Miguel Tomá ; s
- 刊名：Journal of the American Chemical Society
- 出版年：2007
- 出版时间：November 21, 2007
- 年：2007
- 卷：129
- 期：46
- 页码：14422 - 14426
- 全文大小：100K
- 年卷期：v.129,no.46(November 21, 2007)
- ISSN：1520-5126
文摘
A broad range of substituted 2-cyclopentenone derivatives 3-6 are synthesized by the nickel(0)-mediated [3 + 2] cyclization reaction of chromium alkenyl(methoxy)carbene complexes 1 and internalalkynes 2. The reaction takes place with complete regioselectivity with both unactivated alkynes and activatedalkynes (electron-withdrawing and electron-donating substituted alkynes). Representative cycloadductscontaining boron and tin substituents are further demonstrated to be active partners in classical Pd-catalyzedC-C coupling processes to allow the production of 2-aryl- and 2-alkynyl-substituted cyclopentenones 9-13.