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(1-甲氧羰基戊二烯基)铁(1+)阳离子与氢化物、甲基和氮亲核试剂的反应活性。

Reactivity of (1-methoxycarbonylpentadienyl)iron(1+) cations with hydride, methyl, and nitrogen nucleophiles.

作者信息

Ma Yuzhi, Yun Young K, Wondergem Nee Lukesh Julie, Sar Anobick, Gone Jayapal Reddy, Lindeman Sergey, Donaldson William A

机构信息

Department of Chemistry, Marquette University, P. O. Box 1881, Milwaukee, WI 53201-1881 USA.

出版信息

Tetrahedron. 2017 Jul 27;73(30):4493-4500. doi: 10.1016/j.tet.2017.06.026. Epub 2017 Jun 15.

Abstract

The reaction of tricarbonyl and (dicarbonyl)triphenylphosphine (1-methoxycarbonyl-pentadientyl)iron(1+) cations and with methyl lithium, NaBHCN, or potassium phthalimide affords (pentenediyl)iron complexes and , while reaction with dimethylcuprate, gave (,-diene)iron complexes and . Oxidatively induced-reductive elimination of gave vinylcyclopropanecarboxylates . The optically active vinylcyclopropane (+)-, prepared from (1)-, undergoes olefin cross-metathesis with excess (+)- to yield (+)-, a C9-C16 synthon for the antifungal agent ambruticin. Alternatively reaction of with methanesulfonamide or trimethylsilylazide gave (,-diene)iron complexes and . Huisgen [3+2] cyclization of the (azidodienyl)iron complex with alkynes afforded triazoles .

摘要

三羰基和(二羰基)三苯基膦(1 - 甲氧基羰基 - 戊二烯基)铁(1 +)阳离子与甲基锂、硼氢化氰钠或邻苯二甲酰亚钾反应生成(戊二烯基)铁配合物,而与二甲基铜锂反应则生成(, - 二烯)铁配合物。通过氧化诱导 - 还原消除反应得到乙烯基环丙烷羧酸酯。由(1) - 制备的光学活性乙烯基环丙烷(+) - 与过量的(+) - 进行烯烃交叉复分解反应,生成(+) - ,这是抗真菌剂安布曲星的一种C9 - C16合成子。另外,与甲磺酰胺或三甲基硅叠氮化物反应生成(, - 二烯)铁配合物。(叠氮二烯基)铁配合物与炔烃的惠斯根[3 + 2]环化反应生成三唑。

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