Cyclopentadienone synthesis by rhodium(I)-catalyzed [3 + 2] cycloaddition reactions of cyclopropenones and alkynes.
Cyclopentadienone synthesis by rhodium(I)-catalyzed [3 + 2] cycloaddition reactions of cyclopropenones and alkynes.
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DOI：
10.1021/ja065868p
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发表时间：
2006-10
影响因子：
15
通讯作者：
P. Wender;Thomas J. Paxton;T. Williams
中科院分区：
文献类型：
--
作者：
P. Wender;Thomas J. Paxton;T. Williams
发现Rh（I）催化的环丙烯酮和炔的[3 + 2]环加成提供了一种高效和区域控制的环丙烯烯酮（CPD）途径，CPD是广泛用于合成天然和非天然产物、治疗先导物、聚合物、树枝状聚合物、装置和抗原呈递支架的结构单元。该方法的通用性进行了探索与23个例子代表了广泛的炔的变化（芳烷基-，二烷基-，杂芳烷基-）和二芳基-以及芳烷基环丙烯酮。该反应通常使用最少的催化剂负载量以高产率进行，并且在所研究的所有情况下以高或完全的区域选择性进行。该反应容易放大以产生克量的环加合物，并提供了一种独特的和通用的CPD路线，否则将难以获得。
The Rh(I)-catalyzed [3 + 2] cycloaddition of cyclopropenones and alkynes is found to provide a highly efficient and regiocontrolled route to cyclopentadienones (CPDs), building blocks of widespread use in the synthesis of natural and non-natural products, therapeutic leads, polymers, dendrimers, devices, and antigen presenting scaffolds. The versatility of the method is explored with 23 examples representing a wide range of alkyne variations (arylalkyl-, dialkyl-, heteroarylalkyl-) and diaryl- as well as arylalkylcyclopropenones. The reactions often proceed in high yield using minimal catalyst loadings and in all cases examined proceed with high or complete regioselectivity. The reaction is readily scalable to produce gram quantities of cycloadduct and provides a unique and versatile route to CPDs that would be otherwise difficult to obtain.