Alkynyliodonium tetrafluoroborates as a good Michael acceptor for an azido group. A stereoselective synthesis of (Z)-(.beta.-azidovinyl)iodonium salts

1988 ◽  
Vol 53 (26) ◽  
pp. 6144-6145 ◽  
Author(s):  
Masahito Ochiai ◽  
Munetaka Kunishima ◽  
Kaoru Fuji ◽  
Yoshimitsu Nagao
Keyword(s):  
Stereoselective Synthesis ◽  
Azido Group ◽  
Iodonium Salts ◽  
Michael Acceptor ◽  
Group A

Stereoselective synthesis of a blood group A type glycopeptide present in human blood mucin

1995 ◽  
Vol 269 (2) ◽  
pp. 227-257 ◽  
Author(s):  
Wallace M. Macindoe ◽  
Hiroyuki Ijima ◽  
Yoshiaki Nakahara ◽  
Tomoya Ogawa
Keyword(s):  
Blood Group ◽  
Human Blood ◽  
Stereoselective Synthesis ◽  
Blood Group A ◽  
Group A

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.

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