Palladium-catalyzed intramolecular asymmetric hydroamination, hydroalkoxylation, and hydrocarbonation of alkynes

被引：133

作者：

Patil, Nitin T. ^{[1
]}

Lutete, Leopold Mpaka ^{[1
]}

Wu, Huanyou ^{[1
]}

Pahadi, Nirmal K. ^{[1
]}

Gridnev, Ilya D. ^{[1
]}

Yamamoto, Yoshinori ^{[1
]}

机构：

[1] Tohoku Univ, Grad Sch Sci, Dept Chem, Sendai, Miyagi 9808578, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2006年 / 71卷 / 11期

关键词：

D O I：

10.1021/jo0603835

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A conceptually novel approach for asymmetric intramolecular hydroamination, hydroalkoxylation and hydrocarbonation of alkynes using chiral palladium catalysts are described. The reactions of the aminoalkynes 5, alkynols 7, and alkynylmethines 9 in the presence of Pd-2(dba)(3)center dot CHCl3/PhCOOH/renorphos 4 in benzene (or benzene-hexane) at 100 degrees C gave the corresponding cyclization products (nitrogen heterocycles 6, oxygen heterocycles 8, and carbocycles 10) in good yields with good enantioselectivities. The origins of enantioselectivities in the hydroamination reaction are discussed based on DFT computations.

引用

页码：4270 / 4279

页数：10

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