Catalytic Asymmetric Vinylogous Conjugate Addition of Butenolide to 2-Ester-Substituted Chromones: Access to Chiral Chromanone Lactones via Trapping of a Copper(I) Enolate by Trimethyl Borate

被引：5

作者：

Cui, Jin ^{[1
,2
]}

Oriez, Raphael ^{[1
]}

Samanta, Sadhanendu ^{[1
]}

Noda, Hidetoshi ^{[1
]}

Watanabe, Takumi ^{[1
]}

Shibasaki, Masakatsu ^{[1
]}

机构：

[1] Inst Microbial Chem BIKAKEN, Tokyo, Tokyo 1410021, Japan

[2] Fudan Univ, Greater Bay Area Inst Precis Med Guangzhou, Ctr Innovat Drug Discovery, Sch Pharm, Shanghai 200437, Peoples R China

来源：

ORGANIC LETTERS | 2023年 / 25卷 / 46期

基金：

日本学术振兴会;

关键词：

D O I：

10.1021/acs.orglett.3c03503

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A copper-catalyzed asymmetric vinylogous conjugate addition of butenolide to 2-ester-substituted chromones is described, and it delivers syn- or anti-chromanone lactones with high stereoselectivities. The enantioselectivity-determining step varied with the use of B-(OMe)(3 )as an additive, resulting in enhanced stereoselectivities, as revealed by density functional theory calculations, which also provided theoretical insight into the origin of the ligand-dependent diastereodivergence.

引用

页码：8367 / 8371

页数：5

共 21 条

[1] Chemistry and Biology of Mycotoxins and Related Fungal Metabolites [J].

Braese, Stefan ;

Encinas, Arantxa ;

Keck, Julia ;

Nising, Carl F. .

CHEMICAL REVIEWS, 2009, 109 (09) :3903-3990

[2] Direct catalytic asymmetric andanti-selective vinylogous addition of butenolides to chromones [J].

Cui, Jin ;

Kumagai, Naoya ;

Watanabe, Takumi ;

Shibasaki, Masakatsu .

CHEMICAL SCIENCE, 2020, 11 (27) :7170-7176

[3] Structures of the Dimeric and Monomeric Chromanones, Gonytolides A-C, Isolated from the Fungus Gonytrichum sp and Their Promoting Activities of Innate Immune Responses [J].

Kikuchi, Haruhisa ;

Isobe, Masato ;

Sekiya, Mizuki ;

Abe, Yuko ;

Hoshikawa, Tsuyoshi ;

Ueda, Kazunori ;

Kurata, Shoichiro ;

Katou, Yasuhiro ;

Oshima, Yoshiteru .

ORGANIC LETTERS, 2011, 13 (17) :4624-4627

[4] Asymmetric synthesis of chromanone lactones via vinylogous conjugate addition of butenolide to 2-ester chromones [J].

Li, Yi ;

Xin, Shuang ;

Weng, Rui ;

Liu, Xiaohua ;

Feng, Xiaoming .

CHEMICAL SCIENCE, 2022, 13 (30) :8871-8875

[5] Supported Lanthanum Borohydride Catalyzes CH Borylation Inside Zeolite Micropores [J].

Li, Yuting ;

Kanbur, Uddhav ;

Cui, Jinlei ;

Wang, Guocang ;

Kobayashi, Takeshi ;

Sadow, Aaron D. ;

Qi, Long .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2022, 61 (15)

[6] Xanthones from Fungi, Lichens, and Bacteria: The Natural Products and Their Synthesis [J].

Masters, Kye-Simeon ;

Braese, Stefan .

CHEMICAL REVIEWS, 2012, 112 (07) :3717-3776

[7] Bile pigments as HIV-1 protease inhibitors and their effects on HIV-1 viral maturation and infectivity in vitro [J].

McPhee, F ;

Caldera, PS ;

Bemis, GW ;

McDonagh, AF ;

Kuntz, ID ;

Craik, CS .

BIOCHEMICAL JOURNAL, 1996, 320 :681-686

[8] Catalytic enantioselective aldol reaction to ketones [J].

Oisaki, Kounosuke ;

Zhao, Dongbo ;

Kanai, Motomu ;

Shibasaki, Masakatsu .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (22) :7164-7165

[9] Syntheses of Dimeric Tetrahydroxanthones with Varied Linkages: Investigation of "Shapeshifting" Properties [J].

Qin, Tian ;

Iwata, Takayuki ;

Ransom, Tanya T. ;

Beutler, John A. ;

Porco, John A., Jr. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (48) :15225-15233

[10]

Qin T, 2015, NAT CHEM, V7, P234, DOI [10.1038/NCHEM.2173, 10.1038/nchem.2173]

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