Stereoselective Synthesis of Tetrasubstituted Furylalkenes via Gold-Catalyzed Cross-Coupling of Enynones with Diazo Compounds

2017 ◽  
Vol 19 (13) ◽  
pp. 3482-3485 ◽  
Author(s):  
Pei Liu ◽  
Jiangtao Sun
Keyword(s):  
Stereoselective Synthesis ◽  
Cross Coupling ◽  
Diazo Compounds

scholarly journals gem-Difluoroolefination of Diazo Compounds with TMSCF3 or TMSCF2Br: Transition-Metal-Free Cross-Coupling of Two Carbene Precursors

2015 ◽  
Vol 137 (45) ◽  
pp. 14496-14501 ◽  
Author(s):  
Mingyou Hu ◽  
Chuanfa Ni ◽  
Lingchun Li ◽  
Yongxin Han ◽  
Jinbo Hu
Keyword(s):  
Transition Metal ◽  
Cross Coupling ◽  
Diazo Compounds ◽  
Metal Free

scholarly journals Towards the total synthesis of chondrochloren A: synthesis of the (Z)-enamide fragment

2020 ◽  
Vol 16 ◽  
pp. 670-673
Author(s):  
Jan Geldsetzer ◽  
Markus Kalesse
Keyword(s):  
Total Synthesis ◽  
Stereoselective Synthesis ◽  
Cross Coupling ◽  
Vinyl Bromide ◽  
Type Coupling ◽  
Chiral Centers

The stereoselective synthesis of the (Z)-enamide fragment of chondrochloren (1) is described. A Buchwald-type coupling between amide 3 and (Z)-bromide 4 was used to generate the required fragment. The employed amide 3 comprising three chiral centers was obtained through a seven-step sequence starting from ᴅ-ribonic acid-1,4-lactone. The (Z)-vinyl bromide 4 is accessible in four steps from 4-hydroxybenzaldehyde. The pivotal cross coupling between both fragments was achieved after extensive experimentation with copper(I) iodide, K2CO3 and N,N′-dimethylethane-1,2-diamine.

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