scholarly journals Asymmetric Synthesis of Cyclic Hydroxy Ketones Derived from Enol Ethers via Sharpless Asymmetric Dihydroxylation. A Study in the Correlation of the Enol Ether Chain Length and Enantioselectivity.

ChemInform ◽  
2004 ◽  
Vol 35 (9) ◽  
Author(s):  
Benjamin F. Marcune ◽  
Sandor Karady ◽  
Paul J. Reider ◽  
Ross A. Miller ◽  
Mirlinda Biba ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Chain Length ◽  
Enol Ether ◽  
Enol Ethers ◽  
Asymmetric Dihydroxylation ◽  
Hydroxy Ketones

.alpha.-Hydroxy ketones in high enantiomeric purity from asymmetric dihydroxylation of enol ethers

1992 ◽  
Vol 57 (19) ◽  
pp. 5067-5068 ◽  
Author(s):  
Tomiki Hashiyama ◽  
Kouhei Morikawa ◽  
K. Barry Sharpless
Keyword(s):  
Enantiomeric Purity ◽  
Enol Ethers ◽  
Asymmetric Dihydroxylation ◽  
Hydroxy Ketones

Pd-Catalyzed Asymmetric Synthesis of α-Hydroxy Ketones, Acids and Esters

Synfacts ◽  
2008 ◽  
Vol 2008 (11) ◽  
pp. 1186-1186
Author(s):  
B. Stoltz ◽  
M. Seto ◽  
J. Roizen
Keyword(s):  
Asymmetric Synthesis ◽  
Hydroxy Ketones

Carbon-carbon bond formation in reactions of PhIO.cntdot.HBF4-silyl enol ether adduct with alkenes or silyl enol ethers

1989 ◽  
Vol 54 (11) ◽  
pp. 2605-2608 ◽  
Author(s):  
V. V. Zhdankin ◽  
M. Mullikin ◽  
Rik Tykwinski ◽  
Bruce Berglund ◽  
Ronald Caple ◽  
...  
Keyword(s):  
Bond Formation ◽  
Enol Ether ◽  
Enol Ethers ◽  
Carbon Bond ◽  
Silyl Enol Ethers ◽  
Carbon Carbon Bond ◽  
Silyl Enol Ether

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.

An Access to Highly Enantioenriched cis-3,5-Disubstituted γ-Lactones from α-Bromoacetate and Silyl Enol Ether

2021 ◽  
Author(s):  
Ha Rim Lee ◽  
Seo Yun Kim ◽  
Min Ji Park ◽  
Yong Sun Park
Keyword(s):  
Nucleophilic Substitution ◽  
Enol Ether ◽  
Enol Ethers ◽  
Silyl Enol Ethers ◽  
Synthetic Strategy ◽  
Silyl Enol Ether

A novel synthetic strategy for highly enantioenriched cis-3,5-disubstituted γ-lactones has been developed by the AgOTf-promoted nucleophilic substitution of α-bromoacetates with silyl enol ethers and subsequent reductive lactonization. The utility of...

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