Palladium-Catalyzed Cascade Intramolecular Cyclization and Allylation of Enynoates with Allylic Alcohols

被引:12
|
作者
Qiu, Sheng-Qi [1 ]
Ahmad, Tanveer [1 ]
Xu, Yun-He [1 ]
Loh, Teck-Peng [1 ,2 ]
机构
[1] Univ Sci & Technol China, Dept Chem, Hefei 230026, Anhui, Peoples R China
[2] Nanyang Technol Univ, Sch Phys & Math Sci, Div Chem & Biol Chem, Singapore 637371, Singapore
来源
JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 84卷 / 11期
基金
中国国家自然科学基金;
关键词
ALPHA-PYRONES; SELECTIVE SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; CONCISE SYNTHESIS; ISOCOUMARINS; ALKYNES; ACID; ALKENYLATION; STEREOCHEMISTRY; FUSALANIPYRONE;
D O I
10.1021/acs.joc.9b00461
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A Pd(II)-catalyzed mild and highly regioselective 6-endo cyclization/allylation reaction of enynoates with simple allylic alcohols has been developed. Under mild reaction conditions, the vinyl palladium species generated in situ after cyclization could insert C-C double bond of allylic alcohol through cross-coupling reaction and lead to the formation of allyl pyrone via beta-OH elimination. This cascade cross-coupling reaction represents a direct and atom economic methodology for the construction of novel allyl pyrones in moderate to good yields.
引用
收藏
页码:6729 / 6736
页数:8
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