First cobalt(I)-catalyzed [6+2] cycloadditions of cycloheptatriene with alkynes

被引：61
|
作者：
Achard, M [1 ]
Tenaglia, A [1 ]
Buono, G [1 ]
机构：
[1] Univ Aix Marseille P Cezanne, Fac Sci & Tech St Jerome, Lab Synth Asymetr, UMR 6180,CNRS Chirotechnol Catalyse & Biocatalyse, F-13397 Marseille, France
来源：
ORGANIC LETTERS | 2005年 / 7卷 / 12期
关键词：
D O I：
10.1021/ol050618j
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The Col(2)(dppe)/Zn/Znl(2) system effectively catalyzes the [6 + 2] cycloaddition of cycloheptatriene with terminal alkynes to afford 7-alkylbicyclo[4.2.1]nona-2,4,7-trienes in fair to excellent yields. The catalyst proved to be tolerant toward functional groups such as ketone, sulfone, ester, ketal, ether, alcohol, imide, and nitrile. The enantioselective cycloaddition of CHT and phenylacetylene with BINOL phosphoramidite ligand 4 afforded the cycloadduct 3a (R = Ph) in 91% yield and 74% ee.
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收藏
页码：2353 / 2356
页数：4
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