4.5 Article

Bronsted Base-Catalyzed Direct 1,6-Conjugate Addition of Butenolide to p-Quinone Methides

Related references

Note: Only part of the references are listed.
Article Chemistry, Organic

Asymmetric Syn-Selective Vinylogous Addition of Butenolides to Chromones via Al-Li-BINOL Catalysis

Sadhanendu Samanta et al.

Summary: A gram-scale syn-selective asymmetric vinylogous addition of butenolides to chromones, catalyzed by an Al-Li-BINOL (ALB) complex, was developed in this study. The diastereoselectivity reached 20:1 with 84-98% ee for various combinations of substrates. This protocol complements previous methods and improves selectivity for multiple chromones.

JOURNAL OF ORGANIC CHEMISTRY (2023)

Article Chemistry, Multidisciplinary

Concise and Stereodivergent Approach to Chromanone Lactones through Copper-Catalyzed Asymmetric Vinylogous Addition of Siloxyfurans to 2-Ester-Substituted Chromones

Jin Cui et al.

Summary: The copper(I)-catalyzed asymmetric vinylogous additions of siloxyfurans to 2-ester-substituted chromones enable concise and enantioselective assembly of chromanone lactones. This method provides a efficient synthesis of chromanone lactones with precise stereochemical control, which can be used for the formal synthesis of secalonic acid A.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

Article Chemistry, Multidisciplinary

Asymmetric synthesis of chromanone lactones via vinylogous conjugate addition of butenolide to 2-ester chromones

Yi Li et al.

Summary: Chiral chromanone lactones are important natural products with significant biological activity. In this study, we developed a direct diastereo- and enantioselective vinylogous conjugate addition of butenolide to 2-ester substituted chromones. The reaction demonstrated good efficiency and selectivity, providing the desired products in high yield and excellent enantioselectivity.

CHEMICAL SCIENCE (2022)

Article Chemistry, Multidisciplinary

Iron(iii)-catalyzed tandem annulation of indolyl-substituted p-quinone methides with ynamides for the synthesis of cyclopenta[b]indoles

Ke-Yin Yu et al.

Summary: The unique reactivity of indolyl-substituted p-QMs as a new type of two-carbon synthon in a novel iron(iii)-catalyzed tandem annulation has been explored for the first time. The (2+2) annulation/retro-4 pi electrocyclization/imino-Nazarov cyclization cascade reaction is characterized by an unusual structural reconstruction of indolyl-substituted p-QMs, leading to the rapid assembly of synthetically important functionalized cyclopenta[b]indoles.

CHEMICAL COMMUNICATIONS (2022)

Article Chemistry, Organic

Hf(OTf)4-Catalyzed 1,6-Conjugate Addition of 2-Alkyl-azaarenes to para-Quinone Methides

Xinyuan Liu et al.

Summary: A carbon-carbon bond formation reaction catalyzed by Hf(OTf)(4) between 2-alkyl-azaarenes and para-quinone methides (p-QMs) was reported, providing rapid access to a variety of triarylethane products in good yields. The catalyst loading could be reduced to 1 mol%. Studies on scale-up reactions and product derivatization were also presented.

JOURNAL OF ORGANIC CHEMISTRY (2021)

Review Chemistry, Multidisciplinary

Deconjugated butenolide: a versatile building block for asymmetric catalysis

Abhijnan Ray Choudhury et al.

CHEMICAL SOCIETY REVIEWS (2020)

Article Chemistry, Multidisciplinary

Direct catalytic asymmetric andanti-selective vinylogous addition of butenolides to chromones

Jin Cui et al.

CHEMICAL SCIENCE (2020)

Review Chemistry, Organic

Recent developments in 1,6-addition reactions ofpara-quinone methides (p-QMs)

Jia-Yin Wang et al.

ORGANIC CHEMISTRY FRONTIERS (2020)

Article Chemistry, Multidisciplinary

Direct Enantio- and Diastereoselective Vinylogous Addition of Butenolides to Chromones Catalyzed by Zn-ProPhenol

Barry M. Trost et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

Article Chemistry, Multidisciplinary

Direct Catalytic Asymmetric Aldol Reaction of Thioamide with an -Vinyl Appendage

Jin Cui et al.

CHEMISTRY-A EUROPEAN JOURNAL (2018)

Review Chemistry, Multidisciplinary

Recent Advances in the Catalytic Enantioselective Reactions of para-Quinone Methides

Wenjun Li et al.

CHEMISTRY-AN ASIAN JOURNAL (2018)

Article Chemistry, Organic

Catalytic asymmetric synthesis of key intermediate for scytophycin C

Jin Cui et al.

TETRAHEDRON LETTERS (2016)

Article Chemistry, Physical

A Career in Catalysis: Masakatsu Shibasaki

Naoya Kumagai et al.

ACS CATALYSIS (2016)

Review Chemistry, Multidisciplinary

Recent Advances in Direct Catalytic Asymmetric Transformations under Proton-Transfer Conditions

Naoya Kumagai et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2011)

Article Chemistry, Multidisciplinary

A Synthesis of Tamiflu by Using a Barium-Catalyzed Asymmetric Diels-Alder-Type Reaction

Kenzo Yamatsugu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2009)

Review Chemistry, Multidisciplinary

Chemistry and Biology of Mycotoxins and Related Fungal Metabolites

Stefan Braese et al.

CHEMICAL REVIEWS (2009)

Review Biochemistry & Molecular Biology

The chemistry of marine furanocembranoids, pseudopteranes, gersolanes, and related natural products

Paul A. Roethle et al.

NATURAL PRODUCT REPORTS (2008)

Review Biotechnology & Applied Microbiology

Novel therapeutic applications of cardiac glycosides

Ioannis Prassas et al.

NATURE REVIEWS DRUG DISCOVERY (2008)

Article Chemistry, Physical

Experimental gas-phase basicity scale of superbasic phosphazenes

Ivari Kaljurand et al.

JOURNAL OF PHYSICAL CHEMISTRY A (2007)

Article Chemistry, Multidisciplinary

Catalytic enantioselective Mannich-type reactions of ketoimines

Yutaka Suto et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2007)

Article Chemistry, Multidisciplinary

Catalytic enantioselective aldol reaction to ketones

Kounosuke Oisaki et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2006)

Review Biochemistry & Molecular Biology

Acetogenins from Annonaceae: recent progress in isolation, synthesis and mechanisms of action

A Bermejo et al.

NATURAL PRODUCT REPORTS (2005)

Article Chemistry, Organic

pKa measurements of P(RNCH2CH3)3N

PB Kisanga et al.

JOURNAL OF ORGANIC CHEMISTRY (2000)