Stereoselective synthesis of the synthons having three consective chiral centers

1983 ◽  
Vol 24 (26) ◽  
pp. 2661-2664 ◽  
Author(s):  
Tadashi Nakata ◽  
Mineo Fukui ◽  
Hisatoshi Ohtsuka ◽  
Takeshi Oishi
Keyword(s):  
Stereoselective Synthesis ◽  
Chiral Centers

Enantioselective Multi-Component Cyclopropane Synthesis Enabled by Cu-Catalyzed Cyclopropene Carbometallation with Organoboron Reagent

2018 ◽  
Author(s):  
Zhanyu Li ◽  
Mengru Zhang ◽  
Yu Zhang ◽  
Shuang Liu ◽  
Jinbo Zhao ◽  
...  
Keyword(s):  
Carbon Source ◽  
Stereoselective Synthesis ◽  
Organometallic Reagents ◽  
Preliminary Results ◽  
Quaternary Center ◽  
Chiral Centers ◽  
Substituted Cyclopropanes ◽  
Proof Of Principle

Deployment of organoboron in lieu of the strongly basic <br>organometallic reagents as carbon source in Cu-catalyzed <br>cyclopropene carbometallation opens unprecedented three-<br>component reactivity for stereoselective synthesis of poly-substituted cyclopropanes. A proof-of-principle demonstration of this novel carbometallation strategy is presented herein for a highly convergent access to poly-substituted aminocyclopropane framework via <br>carboamination. Preliminary results on asymmetric desymmetrization with commercial bisphosphine ligands attained high levels of enantioselection, offering a straightforward access to enantioenriched aminocyclopropanes bearing all-three chiral centers, including an all-carbon quaternary center. This strategy may underpin a host of novel synthetic protocols for poly-substituted cyclopropanes. <br>

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.

Acetic acid promoted tandem cyclization of in situ generated 1,3-dipoles: stereoselective synthesis of dispiroimidazolidinyl and dispiropyrrolidinyl oxindoles with multiple chiral stereocenters

RSC Advances ◽  
2015 ◽  
Vol 5 (97) ◽  
pp. 79413-79422 ◽  
Author(s):  
Koorathota Suman ◽  
Sathiah Thennarasu
Keyword(s):  
Acetic Acid ◽  
Stereoselective Synthesis ◽  
Single Step ◽  
Pyrrolidine Ring ◽  
Acid Catalyzed ◽  
Chiral Centers ◽  
Tandem Cyclization

Acetic acid catalyzed in situ generation of ketimine based 1,3-dipoles, and single-step construction of imidazolidine ring with three chiral centers and pyrrolidine ring with four chiral centers via formation of new C–N and C–C bonds is reported.

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