Diastereoselective epoxide rearrangements using lithium amide bases: first stereocontrolled synthesis of 4-deoxyconduritols

2000 ◽  
pp. 1521-1522 ◽  
Author(s):  
Alex Kee ◽  
Peter O’Brien ◽  
Christopher D. Pilgram ◽  
Simon T. Watson
Keyword(s):  
Lithium Amide ◽  
Stereocontrolled Synthesis

ChemInform Abstract: Diastereoselective Epoxide Rearrangements Using Lithium Amide Bases: First Stereocontrolled Synthesis of 4-Deoxyconduritols.

ChemInform ◽  
2000 ◽  
Vol 31 (49) ◽  
pp. no-no
Author(s):  
Alex Kee ◽  
Peter O'Brien ◽  
Christopher D. Pilgram ◽  
Simon T. Watson
Keyword(s):  
Lithium Amide ◽  
Stereocontrolled Synthesis

scholarly journals Lithium-mediated Ferration of Fluoroarenes

2020 ◽  
Vol 74 (11) ◽  
pp. 866-870
Author(s):  
Lewis C. H. Maddock ◽  
Alan Kennedy ◽  
Eva Hevia
Keyword(s):  
Hydrogen Atom ◽  
Organometallic Chemistry ◽  
Room Temperature ◽  
Structural Elucidation ◽  
Side Reactions ◽  
Metal Base ◽  
Lithium Amide ◽  
Mixed Metal ◽  
Important Challenge

While fluoroaryl fragments are ubiquitous in many pharmaceuticals, the deprotonation of fluoroarenes using organolithium bases constitutes an important challenge in polar organometallic chemistry. This has been widely attributed to the low stability of the in situ generated aryl lithium intermediates that even at –78 °C can undergo unwanted side reactions. Herein, pairing lithium amide LiHMDS (HMDS = N{SiMe3}2) with FeII(HMDS)2 enables the selective deprotonation at room temperature of pentafluorobenzene and 1,3,5-trifluorobenzene via the mixed-metal base [(dioxane)LiFe(HMDS)3] (1) (dioxane = 1,4-dioxane). Structural elucidation of the organometallic intermediates [(dioxane)Li(HMDS)2Fe(ArF)] (ArF = C6F5, 2; 1,3,5-F3-C6H2, 3) prior electrophilic interception demonstrates that these deprotonations are actually ferrations, with Fe occupying the position previously filled by a hydrogen atom. Notwithstanding, the presence of lithium is essential for the reactions to take place as Fe II (HMDS)2 on its own is completely inert towards the metallation of these substrates. Interestingly 2 and 3 are thermally stable and they do not undergo benzyne formation via LiF elimination.

Stereocontrolled synthesis of tetrahydrofurans and tetrahydropyrans using thallium(III)-induced cyclizations

1985 ◽  
Vol 50 (14) ◽  
pp. 2416-2423 ◽  
Author(s):  
Joseph P. Michael ◽  
Pauline C. Ting ◽  
Paul A. Bartlett
Keyword(s):  
Stereocontrolled Synthesis

scholarly journals Compositional flexibility in Li-N-H materials: implications for ammonia catalysis and hydrogen storage.

2021 ◽  
Author(s):  
Joshua Makepeace ◽  
Jake M Brittain ◽  
Alisha Sukhwani Manghnani ◽  
Claire Murray ◽  
Thomas J Wood ◽  
...  
Keyword(s):  
Energy Storage ◽  
Hydrogen Storage ◽  
Compositional Variation ◽  
Lithium Amide ◽  
Lithium Imide ◽  
Energy Storage Applications

Li-N-H materials, particularly lithium amide and lithium imide, have been explored for use in a variety of energy storage applications in recent years. Compositional variation within the parent lithium imide,...

scholarly journals Solid-Phase Stereocontrolled Synthesis of Oligomeric P-Modified Glycosyl Phosphate Derivatives Using the Oxazaphospholidine Method

ACS Omega ◽  
2021 ◽  
Author(s):  
Kazuki Sato ◽  
Tomoya Hagio ◽  
Michi Sano ◽  
Kazumasa Muramoto ◽  
Aya Yaoita ◽  
...  
Keyword(s):  
Solid Phase ◽  
Stereocontrolled Synthesis ◽  
Glycosyl Phosphate

ChemInform Abstract: A Facile and Stereocontrolled Synthesis of syn-α-Alkyl α-Hydroxy β-Amino Acids.

ChemInform ◽  
2010 ◽  
Vol 31 (5) ◽  
pp. no-no
Author(s):  
Alessandra Maria Nocioni ◽  
Carmela Papa ◽  
Claudia Tomasini
Keyword(s):  
Amino Acids ◽  
Stereocontrolled Synthesis
Sign in / Sign up

Export Citation Format

Share Document