Desymmetrization of Diolefinic Diols by Enantioselective Amino‐thiocarbamate‐Catalyzed Bromoetherification: Synthesis of Chiral Spirocycles

Tay, Daniel Weiliang; Leung, Gulice Y. C.; Yeung, Ying‐Yeung

doi:10.1002/anie.201310136

Cited by 91 publications

(16 citation statements)

References 74 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In particular, recently antitumor [4], anesthetic [5] and enzyme inhibitory effects were discovered, including HIV-1 reverse transcriptase inhibition activity [6–11]. Moreover, their utilization as highly regio- and stereoselective organocatalysts in specific types of chemical tranformations [12–17] was introduced, as well. More recently, O -thiocarbamates have been used as H 2 S donors in biological systems [18] and as intermediates in pharmaceutically significant organic syntheses [19–20].…”

Section: Introductionmentioning

confidence: 99%

A novel three-component reaction between isocyanides, alcohols or thiols and elemental sulfur: a mild, catalyst-free approach towards O-thiocarbamates and dithiocarbamates

Németh¹,

Keserü²,

Ábrányi‐Balogh³

2019

Beilstein J. Org. Chem.

View full text Add to dashboard Cite

A new multicomponent reaction has been developed between isocyanides, sulfur and alcohols or thiols under mild reaction conditions to afford O-thiocarbamates and dithiocarbamates in moderate to good yields. The one-pot reaction cascade involves the formation of an isothiocyanate intermediate, thus a catalyst-free synthesis of isothiocyanates, as valuable building blocks from isocyanides and sulfur is proposed, as well. The synthetic procedure suits the demand of a modern organic chemist, as it tolerates a wide range of functional groups, it is atom economic and easily scalable.

show abstract

Section: Introductionmentioning

confidence: 99%

A novel three-component reaction between isocyanides, alcohols or thiols and elemental sulfur: a mild, catalyst-free approach towards O-thiocarbamates and dithiocarbamates

Németh¹,

Keserü²,

Ábrányi‐Balogh³

2019

Beilstein J. Org. Chem.

View full text Add to dashboard Cite

show abstract

“…45 The process works in two steps: a first bromoetherification catalyzed by a quinidine derivative allows the desymmetrization, and then a second bromoetherification occurs, with the stereoselectivity controlled by the stereogenic centers formed during the first step (Scheme 13).…”

Section: Scheme 12: Rationalization Of the Enantioselectivity In The mentioning

confidence: 99%

Recent advances in the synthesis of tetrahydrofurans and applications in total synthesis

et al. 2016

View full text Add to dashboard Cite

Mousseron. His research interests include the total synthesis of oxygenated cyclic and non cyclic metabolites of polyunsaturated fatty acids, mainly leukotrienes, iso-, phyto-and neuroprostanes, as well as dihydroxylated PUFAs and more recently lipophenols and the understanding of the role of such bioactive lipids and lipophenols by developing collaborations with chemists, biochemists, biologists and clinicians across the world. Jean-Marie Galano studied chemistry at Paul Cézanne Université Marseille and obtained his PhD under the supervision of Honoré Monti in 2001. He then moved to the University of Oxford to pursue a postdoctoral fellowship with David H. Hodgson on the development of new methods for the total synthesis of natural products. In October 2005 he joined the CNRS as a Chargé de Recherche at Université of Montpellier. His research focuses on the total synthesis and discovery of new lipid metabolites, and to discover their potential implications in human health. AbstractMany natural products contain tetrahydrofuran (THF) moieties. Those molecules, often biologically active, may be structurally diverse, e.g. cis or trans THF, mono-, di-, tri-or tetrasubstituted on the furan ring. Thus, the construction of THF is of great interest for the community of organic chemists; especially in developing new methodologies, and applying them in the total synthesis of natural products. The aim of this review is to report recent advances in the field of THF synthesis, as well as the application of these methods to the synthesis of bioactive compounds.

show abstract

“…Yeung et al. reported enantioselective desymmetrizing bromoetherification reactions of olefinic 1,3‐diols catalyzed by a quinidine derived amino‐thiocarbamate4b or a C 2 symmetric sulfide 4c…”

Section: Optimization Of the Reaction Conditions[a]mentioning

confidence: 99%

Gold(I)‐Catalyzed Enantioselective Desymmetrization of 1,3‐Diols through Intramolecular Hydroalkoxylation of Allenes

Toste

2015

Angew Chem Int Ed

View full text Add to dashboard Cite

A gold(I)-catalyzed enantioselective desymmetrization of 1,3-diols was achieved via intramolecular hydroalkoxylation of allenes. The catalyst system 3-F-dppe(AuCl)2/(R)-C8-TRIPAg proved to be specifically efficient to promote the desymmetrizing cyclization of 2-aryl-1,3-diols, which have proven challenging substrates in previous reports. Multisubstituted tetrahydrofurans were prepared in good yield with good enantioselectivity and diastereoselectivity by this method.

show abstract

Desymmetrization of Diolefinic Diols by Enantioselective Amino‐thiocarbamate‐Catalyzed Bromoetherification: Synthesis of Chiral Spirocycles

Cited by 91 publications

References 74 publications

A novel three-component reaction between isocyanides, alcohols or thiols and elemental sulfur: a mild, catalyst-free approach towards O-thiocarbamates and dithiocarbamates

A novel three-component reaction between isocyanides, alcohols or thiols and elemental sulfur: a mild, catalyst-free approach towards O-thiocarbamates and dithiocarbamates

Recent advances in the synthesis of tetrahydrofurans and applications in total synthesis

Gold(I)‐Catalyzed Enantioselective Desymmetrization of 1,3‐Diols through Intramolecular Hydroalkoxylation of Allenes

Contact Info

Product

Resources

About