Rhodium(I)-Catalyzed Intermolecular [2+2+2] Cycloaddition of Allenyl Aldehydes with Alkynes and Related Cyclization

Rhodium(I)-Catalyzed Intermolecular [2+2+2] Cycloaddition of Allenyl Aldehydes with Alkynes and Related Cyclization
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铑(I)催化的分子间[2 2 2]烯醛与炔烃的环加成及相关环化

DOI:
10.1002/ajoc.201402239
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发表时间:
2015
期刊:
Asian J. Org. Chem.
影响因子:
--
通讯作者:
Yoshihiro Sato
Yoshihiro Sato
中科院分区:
--
文献类型:
--
作者:
Yoshihiro Oonishi;Akira Saito;Yoshihiro Sato

文献摘要

相似文献

研究了铑(I)催化联烯醛与各种炔的环化反应。具有富电子芳环和末端吸电子基团的内炔的环化以良好的产率提供[2+2+2]环加成产物,具有良好到高的区域和对映选择性,而末端炔的反应以良好的产率得到二烯基酮而不是[2+2+2]环加成产物。这些结果表明,炔的性质对反应过程有很大的影响。
Rhodium(I)‐catalyzed cyclization of allenyl aldehydes with various alkynes was investigated. The cyclizations of internal alkynes that have both an electron‐rich aromatic ring and an electron‐withdrawing group at the terminus afforded [2+2+2] cycloaddition products in good yields with good to high regio‐ and enantioselectivity, while the reactions of terminal alkynes gave dienyl ketones instead of [2+2+2] cycloaddition products in good yields. These results indicate that the nature of the alkynes greatly influences the reaction course.