Cooperative Tertiary Amine/Palladium-Catalyzed Sequential [4+3] Cyclization/[1,3]-Rearrangement for Stereoselective Synthesis of Spiro [Methylenecyclopentane-1,3′-oxindolines]

被引:10
|
作者
Chen, Yue-You [1 ]
Zhou, Chen-Dong [1 ]
Li, Xing-Tong [1 ]
Yang, Ting-You [1 ]
Han, Wen-Yong [1 ]
Wan, Nan-Wei [1 ]
Chen, Yong-Zheng [1 ]
Cui, Bao-Dong [1 ]
机构
[1] Zunyi Med Univ, Sch Pharm & Key Lab Basic Pharmacol Minist Educ &, Key Lab Biocatalysis & Chiral Drug Synth Guizhou P, Zunyi 563000, Peoples R China
来源
JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 01期
关键词
BAYLIS-HILLMAN CARBONATES; CONIA-ENE; TRANSITION-METAL; ENANTIOSELECTIVE CONSTRUCTION; QUATERNARY CARBONS; ALPHA-ALLYLATION; NATURAL-PRODUCTS; CYCLOADDITION; STEREOCENTERS; ANNULATION;
D O I
10.1021/acs.joc.2c02393
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A cooperative tertiary amine/palladium-catalyzed sequential reaction process, proceeding via a [4 + 3] cyclization of isatin-derived Morita-Baylis-Hillman Expansion (MBH) carbonates and tert-butyl 2-(hydroxymethyl)allyl carbonates followed by a [1,3]-rearrangement, has been found and developed. A range of structurally diverse spiro[methylene cyclopentane-1,3 '-oxindo-lines] bearing two adjacent beta,gamma-acyl quaternary carbon stereo-centers, which are difficult to obtain by conventional strategies, were obtained in good yields. Further synthetic utility of this protocol is highlighted by its excellent regio-and stereocontrol as well as the large-scale synthesis and diverse functional transformations of the synthetic compounds. Moreover, the control experiments probably established the plausible mechanism for this sequential [4 + 3] cyclization/[1,3]-rearrangement process.
引用
收藏
页码:371 / 383
页数:13
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