ChemInform Abstract: Stereoselective Synthesis of Five and/or Six Membered Ring Hydroxylactones Obtained by Lewis Acid Mediated Reaction of γ,. delta.-Epoxy-β-hydroxyesters; Access to 5-Methylated 2- Deoxysugars.

ChemInform ◽  
2010 ◽  
Vol 28 (18) ◽  
pp. no-no
Author(s):  
K. NACRO ◽  
M. BALTAS ◽  
J.-M. ESCUDIER ◽  
L. GORRICHON
Keyword(s):  
Lewis Acid ◽  
Stereoselective Synthesis ◽  
Membered Ring

Stereoselective Synthesis of C-Ketosides by Lewis Acid Catalyzed C-Glycosylation of Alkynyl-Ketoses.

ChemInform ◽  
2003 ◽  
Vol 34 (14) ◽  
Author(s):  
Ana M. Gomez ◽  
Clara Uriel ◽  
Serafin Valverde ◽  
Slawomir Jarosz ◽  
J. Cristobal Lopez
Keyword(s):  
Lewis Acid ◽  
Stereoselective Synthesis ◽  
Acid Catalyzed

scholarly journals Addition of lithiated enol ethers to nitrones and subsequent Lewis acid induced cyclizations to enantiopure 3,6-dihydro-2H-pyrans – an approach to carbohydrate mimetics

2010 ◽  
Vol 6 ◽  
Author(s):  
Fabian Pfrengle ◽  
Hans-Ulrich Reissig
Keyword(s):  
Lewis Acid ◽  
Functional Group ◽  
Tricarboxylic Acid ◽  
Membered Ring ◽  
Enol Ether ◽  
Enol Ethers ◽  
Acidic Conditions ◽  
Hydroxylamine Derivatives

A stereodivergent synthesis of enantiopure 3,6-dihydro-2H-pyrans is presented. The addition of lithiated enol ethers to carbohydrate-derived nitrones afforded syn- or anti-configured hydroxylamine derivatives 4a–d that were cyclized under Lewis acidic conditions to yield functionalized dihydropyrans cis- or trans-5a–d containing an enol ether moiety. This functional group was employed for a variety of subsequent reactions such as dihydroxylation or bromination. Bicyclic enol ether 19 was oxidatively cleaved to provide the highly functionalized ten-membered ring lactone 20. The synthesized enantiopure aminopyrans 24, 26, 28 and 30 can be regarded as carbohydrate mimetics. Trimeric versions of 24 and 28 were constructed via their attachment to a tricarboxylic acid core.

Counterion effects in the catalytic stereoselective synthesis of 2,3′-pyrrolidinyl spirooxindoles

2014 ◽  
Vol 50 (40) ◽  
pp. 5242-5244 ◽  
Author(s):  
Jacob P. MacDonald ◽  
Benjamin H. Shupe ◽  
John D. Schreiber ◽  
Annaliese K. Franz
Keyword(s):  
Lewis Acid ◽  
Stereoselective Synthesis ◽  
Acid Catalyzed

A Lewis acid-catalyzed stereoselective [3+2] annulation of crotylsilanes with iminooxindoles is reported to access 2,3′-pyrrolidinyl spirooxindoles with four stereocenters.

A Lewis Acid Catalyzed Intramolecular [4 + 3] Cycloaddition Route to Polycyclic Systems that Contain a Seven-Membered Ring.

ChemInform ◽  
2005 ◽  
Vol 36 (14) ◽  
Author(s):  
Gildas Prie ◽  
Natacha Prevost ◽  
Heather Twin ◽  
Stephanie A. Fernandes ◽  
Jerome F. Hayes ◽  
...  
Keyword(s):  
Lewis Acid ◽  
Membered Ring ◽  
Acid Catalyzed

Intercepting the Nazarov Oxyallyl Intermediate with α-Formyl­vinyl Anion Equivalents to Access Formal Morita–Baylis–Hillman Alkylation Products

Synlett ◽  
2017 ◽  
Vol 28 (12) ◽  
pp. 1486-1490 ◽  
Author(s):  
F. West ◽  
Yen-Ku Wu ◽  
Rongrong Lin
Keyword(s):  
Lewis Acid ◽  
Stereoselective Synthesis ◽  
Domino Reaction ◽  
Alkylation Process ◽  
Acid Catalyzed

A Lewis acid catalyzed cationic domino reaction involving sequential electrocyclization and polar addition of allenol ethers onto the resulting oxyallyl species is described. The overall sequence allows a highly stereoselective synthesis of densely substituted cyclopentanoid compounds containing α-formylvinyl functionality which is formally equivalent to products of a Morita–Baylis–Hillman alkylation process.

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