ChemInform Abstract: GENERAL SYNTHESIS OF OPTICALLY ACTIVE 4-ALKYL (OR ALKENYL)-Γ-LACTONES FROM GLUTAMIC ACID ENANTHIOMERS

1977 ◽  
Vol 8 (21) ◽  
pp. no-no
Author(s):  
U. RAVID ◽  
R. M. SILVERSTEIN
Keyword(s):  
Glutamic Acid ◽  
Optically Active ◽  
General Synthesis

α-Phosphoryl sulfoxides. XI. Sulfenylation of α-phosphoryl sulfoxides and a general synthesis of optically active ketene dithioacetal mono-S-oxides

Tetrahedron ◽  
1997 ◽  
Vol 53 (8) ◽  
pp. 2959-2972 ◽  
Author(s):  
Marian Mikołajczyk ◽  
Wanda H. Midura ◽  
Blanka Wladislaw ◽  
Francisco C. Biaggio ◽  
Liliana Marzorati ◽  
...  
Keyword(s):  
Optically Active ◽  
Ketene Dithioacetal ◽  
General Synthesis

scholarly journals General Synthesis of Cyclopropanols via Organometallic Addition to 1-Sulfonylcyclopropanols as Cyclopropanone Precursors

2020 ◽  
Author(s):  
Roger Machín Rivera ◽  
Yujin Jang ◽  
Christopher M. Poteat ◽  
Vincent Lindsay
Keyword(s):  
Optically Active ◽  
Organometallic Reagents ◽  
Tertiary Alcohols ◽  
Mild Conditions ◽  
Synthetic Approaches ◽  
General Synthesis

The addition of organometallic reagents to ketones constitutes one of the most straightforward synthetic approaches to tertiary alcohols. However, due to the absence of a well-behaved class of cyclopropanone surrogates accessible in enantioenriched form, such a trivial synthetic disconnection has only received very little attention in the literature for the formation of tertiary cyclopropanols. In this work, we report a simple and high-yielding synthesis 1-substituted cyclopropanols via the addition of diverse organometallic reagents to 1- phenylsulfonylcyclopropanols, acting here as in situ precursors of the corresponding cyclopropanones.The transformation is shown to be amenable to sp, sp2 or sp3 -hybridized organometallic C-nucleophiles under mild conditions, and the use of enantioenriched substrates led to highly diastereoselective additions and the formation of optically active cyclopropanols.

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