Synthesis of α‐Quaternary Aldehydes via a Stereoselective Semi‐Pinacol Rearrangement of Optically Active Epoxy Alcohols

2019 ◽  
Vol 8 (8) ◽  
pp. 1390-1393
Author(s):  
Naomichi Hirama ◽  
Ryu Sakamoto ◽  
Keiji Maruoka
Keyword(s):  
Optically Active ◽  
Pinacol Rearrangement ◽  
Epoxy Alcohols

Highly Stereoselective Synthesis of Optically Active α,β-Epoxy Alcohols

1983 ◽  
Vol 13 (11) ◽  
pp. 901-904 ◽  
Author(s):  
S. Banfi ◽  
S. Colonna ◽  
H. Molinari ◽  
S. Julia
Keyword(s):  
Stereoselective Synthesis ◽  
Optically Active ◽  
Epoxy Alcohols

ChemInform Abstract: Synthesis of Optically Active γ-Cyano β,γ-Epoxy Alcohols and Secondary γ-Cyano Allylic Alcohols.

ChemInform ◽  
2010 ◽  
Vol 23 (7) ◽  
pp. no-no
Author(s):  
I. YAMAKAWA ◽  
H. URABE ◽  
Y. KOBAYASHI ◽  
F. SATO
Keyword(s):  
Optically Active ◽  
Allylic Alcohols ◽  
Epoxy Alcohols

The Hudrlik–Peterson Reaction of Secondary cis-TMS-Epoxy Alcohols and its Application to the Synthesis of the Fatty Acid Intermediates

Synlett ◽  
2019 ◽  
Vol 30 (09) ◽  
pp. 1085-1089 ◽  
Author(s):  
Shun Saito ◽  
Yutaro Nanba ◽  
Masao Morita ◽  
Yuichi Kobayashi
Keyword(s):  
Fatty Acid ◽  
Leukotriene B4 ◽  
Optically Active ◽  
Trans Isomers ◽  
Synthetic Intermediates ◽  
Maresin 1 ◽  
Epoxy Alcohols

As an extension of the study on the Hudrlik–Peterson reaction of trans-TMS-epoxy alcohols with lithium acetylides, four cis-TMS-epoxy alcohols possessing different alkyl substituents were subjected to the reaction with TMS-acetylide. The reaction completed in 1 h at 0 °C to afford cis-enynyl alcohols in good yields. The results indicated that cis-TMS-epoxy alcohols had higher reactivity than the trans-isomers. Anions derived from 1-heptyne and phenylacetylene participated in the reaction as well. The reaction was applied to optically active cis-TMS-epoxy alcohols, and the resulting enynyl alcohols were transformed to the synthetic intermediates of protectin D1, maresin 1, resolvin E1, and leukotriene B4.

Kinetics of the acid-catalysed hydration of prop-2-en-1-ol. Evidence for a free, ion-dipole intermediate in the heterolysis of propane-1,2-diol

1982 ◽  
Vol 35 (11) ◽  
pp. 2221 ◽  
Author(s):  
KP Herlihy
Keyword(s):  
Activation Parameters ◽  
Optically Active ◽  
First Order ◽  
Aqueous Acid ◽  
First Order Kinetics ◽  
Pinacol Rearrangement ◽  
Free Ion ◽  
Pseudo First Order ◽  
Kinetics Of ◽  
Good Agreement

Prop-2-en-1-ol in aqueous acid solution gives propane-1,2-diol and propanal. At 100�C the amount of diol in this product ratio is found to decrease from 65% in 1 M HClO4 to 50% in 4 M HClO4. Pseudo-first-order kinetics are found to apply. The values obtained for the activation parameters, Ea and ΔS‡ and for a Hammett acidity plot, are similar to results reported for other alkenes. The relative rates of partitioning between regeneration of the substrate and rearrangement for the pinacol rearrangement of optically active propane-1,2-diol have been calculated previously. When these are compared with product ratios obtained from the hydration of prop-2-en-1-ol, good agreement is found between the respective values if it is assumed that the regenerated substrate has undergone complete racemization of configuration. This is interpreted to be evidence for a short-lived, but free ion-dipole as the intermediate in the heterolysis of propane-1,2-diol.

Synthesis of optically active γ-cyano-β, γ-epoxy alcohols and secondary γ-cyano allylic alcohols

1991 ◽  
Vol 32 (18) ◽  
pp. 2045-2048 ◽  
Author(s):  
Isao Yamakawa ◽  
Hirokazu Urabe ◽  
Yuichi Kobayashi ◽  
Fumie Sato
Keyword(s):  
Optically Active ◽  
Allylic Alcohols ◽  
Epoxy Alcohols

Asymmetric Synthesis of Optically Active Epoxy-Alcohols from Achiral Tiglic and Angelic Acid

2010 ◽  
Vol 91 (5) ◽  
pp. 493-493
Author(s):  
Milutin Stefanović ◽  
Ivana Aljančić-Šolaja ◽  
Bogdan Šolaja
Keyword(s):  
Asymmetric Synthesis ◽  
Optically Active ◽  
Angelic Acid ◽  
Epoxy Alcohols
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