ChemInform Abstract: Stereoselective Synthesis of Tricyclic Compounds by Intramolecular Palladium-Catalyzed Addition of Aryl Iodides to Carbonyl Groups.

ChemInform ◽  
2016 ◽  
Vol 47 (36) ◽  
Author(s):  
Jakub Saadi ◽  
Christoph Bentz ◽  
Kai Redies ◽  
Dieter Lentz ◽  
Reinhold Zimmer ◽  
...  
Keyword(s):  
Stereoselective Synthesis ◽  
Carbonyl Groups ◽  
Aryl Iodides ◽  
Tricyclic Compounds ◽  
Palladium Catalyzed

scholarly journals Stereoselective synthesis of tricyclic compounds by intramolecular palladium-catalyzed addition of aryl iodides to carbonyl groups

2016 ◽  
Vol 12 ◽  
pp. 1236-1242 ◽  
Author(s):  
Jakub Saadi ◽  
Christoph Bentz ◽  
Kai Redies ◽  
Dieter Lentz ◽  
Reinhold Zimmer ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Stereoselective Synthesis ◽  
Carbonyl Groups ◽  
Relative Configuration ◽  
X Ray ◽  
Cyclization Process ◽  
Tricyclic Compounds ◽  
Methoxycarbonyl Group ◽  
Palladium Catalyzed ◽  
Group A

Starting from γ-ketoesters with an o-iodobenzyl group we studied a palladium-catalyzed cyclization process that stereoselectively led to bi- and tricyclic compounds in moderate to excellent yields. Four X-ray crystal structure analyses unequivocally defined the structure of crucial cyclization products. The relative configuration of the precursor compounds is essentially transferred to that of the products and the formed hydroxy group in the newly generated cyclohexane ring is consistently in trans-arrangement with respect to the methoxycarbonyl group. A transition-state model is proposed to explain the observed stereochemical outcome. This palladium-catalyzed Barbier-type reaction requires a reduction of palladium(II) back to palladium(0) which is apparently achieved by the present triethylamine.

scholarly journals Palladium-catalyzed three-component tandem reaction of sulfonyl hydrazones, aryl iodides and allenes: highly stereoselective synthesis of (Z)-α-hydroxymethyl allylic sulfones

RSC Advances ◽  
2017 ◽  
Vol 7 (79) ◽  
pp. 50372-50377 ◽  
Author(s):  
Yunlei Hou ◽  
Qi Shen ◽  
Liangyu Zhu ◽  
Yufei Han ◽  
Yanfang Zhao ◽  
...  
Keyword(s):  
Stereoselective Synthesis ◽  
Tandem Reaction ◽  
Aryl Iodides ◽  
Palladium Catalyzed

Sulfonyl hydrazones have been identified as an excellent sulfonyl anion surrogate in the tandem reaction with aryl iodides and allenes for the synthesis of functionalized (Z)-allylic sulfones.

Regio- and stereoselective synthesis of conjugated trienes from silaborated 1,3-enynes

2016 ◽  
Vol 40 (7) ◽  
pp. 6340-6346 ◽  
Author(s):  
Ende Li ◽  
Hui Zhou ◽  
Victor Östlund ◽  
Robin Hertzberg ◽  
Christina Moberg
Keyword(s):  
Stereoselective Synthesis ◽  
Aryl Iodides ◽  
Palladium Catalyzed ◽  
Conjugated Trienes

Palladium-catalyzed silaboration of 1,3-enynes followed by Suzuki–Miyaura coupling with alkenyl iodides and Hiyama coupling with aryl iodides provides access to 1,3,5-trienes with defined regio- and stereochemistry.

Sign in / Sign up

Export Citation Format

Share Document