Quaternary Stereocenters:  Challenges and Solutions for Organic Synthesis Edited by Jens Christoffers and Angelika Baro (Universität Stuttgart). Wiley-VCH Verlag GmbH & Co. KGA:  Weinheim. 2005. xxiv + 336 pp. $170. ISBN 3-527-31107-6.

2006 ◽  
Vol 128 (24) ◽  
pp. 8095-8095 ◽  
Author(s):  
Tomislav Rovis
Keyword(s):  
Organic Synthesis ◽  
Quaternary Stereocenters

Stereodivergent synthesis of 1,4-dicarbonyls by traceless charge–accelerated sulfonium rearrangement

Science ◽  
2018 ◽  
Vol 361 (6403) ◽  
pp. 664-667 ◽  
Author(s):  
Dainis Kaldre ◽  
Immo Klose ◽  
Nuno Maulide
Keyword(s):  
Natural Products ◽  
Double Bond ◽  
Carbonyl Group ◽  
Organic Synthesis ◽  
Relative Configuration ◽  
Chiral Induction ◽  
Tremendous Importance ◽  
Acid Catalyzed ◽  
Quaternary Stereocenters ◽  
Drug Scaffolds

The chemistry of the carbonyl group is essential to modern organic synthesis. The preparation of substituted, enantioenriched 1,3- or 1,5-dicarbonyls is well developed, as their disconnection naturally follows from the intrinsic polarity of the carbonyl group. By contrast, a general enantioselective access to quaternary stereocenters in acyclic 1,4-dicarbonyl systems remains an unresolved problem, despite the tremendous importance of 2,3-substituted 1,4-dicarbonyl motifs in natural products and drug scaffolds. Here we present a broad enantioselective and stereodivergent strategy to access acyclic, polysubstituted 1,4-dicarbonyls via acid-catalyzed [3,3]-sulfonium rearrangement starting from vinyl sulfoxides and ynamides. The stereochemistry at sulfur governs the absolute sense of chiral induction, whereas the double bond geometry dictates the relative configuration of the final products.

Palladium-Catalyzed Cascade Carbonylative Annulation between Alkene-tethered Aryl Iodides and Carbon Monoxide

2021 ◽  
Author(s):  
Yong Zhang ◽  
Ya-Kui Sun ◽  
Ya-Ping Chang ◽  
Hui Shao ◽  
Yu-Ming Zhao
Keyword(s):  
Carbon Monoxide ◽  
Organic Synthesis ◽  
Aryl Iodides ◽  
Rapid Construction ◽  
Palladium Catalyzed ◽  
Quaternary Stereocenters

Rapid construction of molecules bearing all-substituted quaternary stereocenters represents a highly significant but challenging task in organic synthesis. Herein, we report a novel Palladium-catalyzed cascade between alkene-tethered aryl iodides and...

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