Tertiary Amine Mediated Tandem Cross-Rauhut-Currier/Acetalization Reactions: Access to Functionalized Spiro-3,4-Dihydropyrans

被引:55
作者
Yao, Weijun [1 ]
Wu, Yihua [1 ]
Wang, Gang [1 ]
Zhang, Yiping [1 ]
Ma, Cheng [1 ]
机构
[1] Zhejiang Univ, Dept Chem, Hangzhou 310027, Zhejiang, Peoples R China
基金
中国国家自然科学基金;
关键词
cross-coupling; cyclization; Lewis bases; Michael addition; tandem reactions; DIELS-ALDER REACTIONS; BAYLIS-HILLMAN REACTION; ENANTIOSELECTIVE SYNTHESIS; CONJUGATE ADDITIONS; MICHAEL ADDITION; CURRIER REACTION; CATALYSIS; CYCLOISOMERIZATION; ORGANOCATALYSIS; CYCLOADDITION;
D O I
10.1002/anie.200905091
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Γ-Proton transfer furnished the highly selective title reaction in which cyclic bhaloenals 1 react with b,g-unsaturated aketoesters 2 to generate functionalized spiro-3,4-dihydro-2H-pyrans 3 having an a-quaternary carbon center and an adjacent vinyl halide group in skeleton. DBU=1,8-diazabicyclo[5.4.0]undec-7-eno, Tos=4-toluenesulfonyl. © 2009 Wiley-VCH Verlag GmbH &. Co. KGaA.
引用
收藏
页码:9713 / 9716
页数:4
相关论文
共 47 条
[41]   Strategies and approaches for constructing 1-oxadecalins [J].
Tang, Yu ;
Oppenheimer, Jossian ;
Song, Zhenlei ;
You, Lingfeng ;
Zhang, Xuejun ;
Hsung, Richard P. .
TETRAHEDRON, 2006, 62 (47) :10785-10813
[42]   Remarkable phosphine-effect on the intramolecular aldol reactions of unsaturated 1,5-diketones: Highly regioselective synthesis of cross-conjugated dienones [J].
Thalji, RK ;
Roush, WR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (48) :16778-16779
[43]   Organocatalytic Michael cycloisomerization of bis(enones): The intramolecular Rauhut-Currier reaction [J].
Wang, LC ;
Luis, AL ;
Agaplou, K ;
Jang, HY ;
Krische, MJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (11) :2402-2403
[44]   Erigeroflavanone, a flavanone derivative from the flowers of Erigeron annuus with protein glycation and aldose reductase inhibitory activity [J].
Yoo, Nam Hee ;
Jang, Dae Sik ;
Yoo, Jeong Lim ;
Lee, Yun Mi ;
Kim, Young Sook ;
Cho, Jung-Hee ;
Kim, Jin Sook .
JOURNAL OF NATURAL PRODUCTS, 2008, 71 (04) :713-715
[45]   Chiral N-Heterocyclic Carbene-Catalyzed Formal [4+2] Cycloaddition of Ketenes with Enones: Highly Enantioselective Synthesis of trans- and cis-δ-Lactones [J].
Zhang, Yan-Rong ;
Lv, Hui ;
Zhou, Di ;
Ye, Song .
CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (28) :8473-8476
[46]  
Zhong C., 2009, ANGEW CHEM, V121, P1305, DOI DOI 10.1002/ANGE.200805558
[47]   Enantioselective Intermolecular Crossed-Conjugate Additions between Nitroalkenes and α,β-Enals through a Dual Activation Strategy [J].
Zhong, Cheng ;
Chen, Yunfeng ;
Petersen, Jeffrey L. ;
Akhmedov, Novruz G. ;
Shi, Xiaodong .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (07) :1279-1282