Palladium-Catalyzed Asymmetric (2+3) Annulation of p-Quinone Methides with Trimethylenemethanes: Enantioselective Synthesis of Functionalized Chiral Spirocyclopentyl p-Dienones

被引：33

作者：

Jia, Zhi-Long ^{[1
]}

An, Xian-Tao ^{[1
]}

Deng, Yu-Hua ^{[2
]}

Wang, Hui-Bin ^{[1
]}

Gan, Kang-Ji ^{[1
]}

Zhang, Jing ^{[1
]}

Zhao, Xian-He ^{[1
]}

Fan, Chun-An ^{[1
]}

机构：

[1] Lanzhou Univ, State Key Lab Appl Organ Chem, Coll Chem & Chem Engn, Lanzhou 730000, Peoples R China

[2] Yunnan Univ, Sch Chem Sci & Technol, Key Lab Med Chem Nat Resource, Minist Educ, Kunming 650091, Yunnan, Peoples R China

来源：

ORGANIC LETTERS | 2020年 / 22卷 / 11期

关键词：

RAUHUT-CURRIER REACTION; 3+2 CYCLOADDITION; 1,6-CONJUGATE ADDITION; ORGANOCATALYTIC 1,6-ADDITION; N-ALKYLATION; CONSTRUCTION; DIHYDROCOUMARINS; PHOSPHORAMIDITE; DEAROMATIZATION; PYRROLIDINES;

D O I：

10.1021/acs.orglett.0c01252

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel asymmetric catalytic (2+3) annulation of p-quinone methides with CN-substituted trimethylene-methane is described under palladium catalysis, providing an alternative approach for the enantioselective construction of highly functionalized chiral spirocyclopentyl p-dienones. Driven by the significant improvement in the reactivity and enantioselectivity, a novel type of non-C-2-symmetric phosphoramidite ligand from the chirality-matched combination of (S)-BINOL and sterically demanding amine derived from L-hydroxyproline is evolved and explored for the protocol presented here.

引用

页码：4171 / 4175

页数：5

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