scholarly journals N-Acyldihydropyridones as Synthetic Intermediates. A Stereoselective Synthesis of Acyclic Amino Alcohols Containing Multiple Chiral Centers

2008 ◽  
Vol 73 (24) ◽  
pp. 9744-9751 ◽  
Author(s):  
W. Stephen McCall ◽  
Teresa Abad Grillo ◽  
Daniel L. Comins
Keyword(s):  
Stereoselective Synthesis ◽  
Amino Alcohols ◽  
Synthetic Intermediates ◽  
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>

Direct Stereoselective Synthesis of Enantiomerically Pure anti-β-Amino Alcohols

2014 ◽  
Vol 79 (15) ◽  
pp. 6775-6782 ◽  
Author(s):  
Gastón Silveira-Dorta ◽  
Osvaldo J. Donadel ◽  
Víctor S. Martín ◽  
José M. Padrón
Keyword(s):  
Stereoselective Synthesis ◽  
Amino Alcohols ◽  
Enantiomerically Pure

Stereoselective synthesis of anti-2-oxazolidinones by Ph3P–CCl4–Et3N mediated SN2 cyclization of N-Boc-β-amino alcohols

2003 ◽  
Vol 44 (33) ◽  
pp. 6323-6325 ◽  
Author(s):  
G Madhusudhan ◽  
G Om Reddy ◽  
J Ramanatham ◽  
P.K Dubey
Keyword(s):  
Stereoselective Synthesis ◽  
Amino Alcohols

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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