A Catalytic Asymmetric Three‐Component 1,4‐Addition/Aldol Reaction: Enantioselective Synthesis of the Spirocyclic System of Vannusal A

Nicolaou, K. C.; Tang, Wenjun; Dagneau, Philippe; Faraoni, Raffaella

doi:10.1002/ange.200500789

Cited by 31 publications

(11 citation statements)

References 27 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…There are many examples in the literature which report enantioselective addition/trapping experiments with cycloalkenones using ionic chemistry to provide 2,3‐disubstituted cycloalkanones. These reactions show selectivities across the spectrum in addition/trapping experiments . Reactions with 2‐substituted cyclohexenones generally proceed with modest enantio‐ and/or diastereoselectivity .…”

Section: Introductionmentioning

confidence: 94%

Asymmetric Synthesis of 2,3‐Disubstituted Cyclic Ketones by Enantioselective Conjugate Radical Additions

Nad

Sibi

2019

Helvetica Chimica Acta

View full text Add to dashboard Cite

show abstract

Section: Introductionmentioning

confidence: 94%

Asymmetric Synthesis of 2,3‐Disubstituted Cyclic Ketones by Enantioselective Conjugate Radical Additions

Nad

Sibi

2019

Helvetica Chimica Acta

View full text Add to dashboard Cite

show abstract

“…A number of other reports have also appeared in the last two years, including the molybdenum carbonyl mediated tandem allenic Pauson-Khand reaction [76] in the presence of CO-the highly enantio-and diastereoselective one-pot synthesis [77] of acyclic epoxy alcohols and allylic epoxy alcohols, the domino ring-opening/rearrangement reaction [78] of 2,3-epoxy-1-alcohols and PIFA(phenyliodine(III) bis(trifluoroacetate)), the tandem [4+2]/1,3-dipolar [3+2] cycloaddition of oxadiazoles [79] that allowed direct access to the pentacyclic aspidosperma skeleton in a reaction cascade forming four new C-C bonds and three new rings, and a catalytic asymmetric three-component 1,4-addition/aldol reaction in the enantioselective synthesis [80] of the spirocyclic moiety of Vannusal A. All these will not be detailed here due to space limitation.…”

Section: Tandem Reactionsmentioning

confidence: 99%

A new era for organic synthesis—highlights of the recent progress

Yikang

2007

Front. Chem. China

View full text Add to dashboard Cite

The major progress in organic synthesis since 2005 is briefly surveyed in two parts. The first part deals with some of the most impressive advances in the synthetic methodology, which includes: (1) metal-mediated synthetic reactions, with an emphasis on the olefin metathesis and gold-mediated reactions; (2) free radical-based organic synthesis; (3) synthetic transformations performed in a "one-pot" manner involving either tandem reactions or multicomponent reactions; (4) asymmetric reactions catalyzed by metal and organo-catalysts. The major advances in total synthesis of some complex natural products with significant biological activities are presented in the second part, with detailed illustrations of ten selected molecules, including dragmacidin F, abyssomicin C, 11-acetoxy-4-deoxyasbestinin D, pentacycloanammoxic acid, UCS1025A, (−)-merrilactone A, nigellamine A 2 , (+)-saxitoxin, and Tamiflu (an artificially designed natural product-like molecule). An array of complicated structures of the natural products synthesized over the last two years is also listed to serve as a convenient lead to the original literature for the prospective interested readers.Keywords organic synthesis, metal-mediated synthetic reaction, free radical reaction, "in one pot" reaction, asymmetric reaction, total synthesis of natural products Organic reactions are of central importance to organic synthetic methodology and underlie all types of organic A new era for organic synthesis-highlights of the recent progress

show abstract

“…8 This clearly shows the importance of metalcatalyzed asymmetric conujugate additions of alkenyl 45 nucleophiles and the development of such methodologies. 50 In this article, we describe the methodologies that have been developed over the last decade for rhodium and copper catalyzed conjugate addition reactions employing alkenyl organometallic reagents. We divided the two main chapters of rhodium and 55 copper catalyzed ACA reactions in subchapters focusing on the different organometallic nucleophiles employed.…”

Section: Introductionmentioning

confidence: 99%

Rhodium and copper-catalyzed asymmetric conjugate addition of alkenyl nucleophiles

Müller

Alexakis

2012

Chem. Commun.

View full text Add to dashboard Cite

Since the initial reports in the mid-90s, metal catalyzed asymmetric conjugate addition (ACA) reactions evolved as an important tool for the synthetic chemist. Most of the research efforts have been done in the field of rhodium and copper catalyzed ACA reactions employing aryl and alkyl nucleophiles. Despite the great synthetic value of the double bond, the addition of alkenyl nucleophiles remains insufficiently explored. In this account, an overview of the developments in the field of rhodium and copper catalyzed ACA reactions with organometallic alkenyl reagents (B, Mg, Al, Si, Zr, Sn) will be provided. The account is intended to give a comprehensive overview of all the existing methods. However, in many cases only selected examples are displayed in order to facilitate comparison of different ligands and methodologies.

show abstract

A Catalytic Asymmetric Three‐Component 1,4‐Addition/Aldol Reaction: Enantioselective Synthesis of the Spirocyclic System of Vannusal A

Cited by 31 publications

References 27 publications

Asymmetric Synthesis of 2,3‐Disubstituted Cyclic Ketones by Enantioselective Conjugate Radical Additions

Asymmetric Synthesis of 2,3‐Disubstituted Cyclic Ketones by Enantioselective Conjugate Radical Additions

A new era for organic synthesis—highlights of the recent progress

Rhodium and copper-catalyzed asymmetric conjugate addition of alkenyl nucleophiles

Contact Info

Product

Resources

About