Publication

A fluoroisoprenylation sequence employing 2-fluoroalkenal derived azomethines as key intermediates: a stereocontrolled synthesis of 2-fluorogeraniol and 2-fluorofarnesol

Manfred Schlosser
1994
Journal Articles

Abstract

Azomethines (Schiff's bases) derived from a,b-unsatd. a-fluoroaldehydes can be deprotonated with lithium diisopropylamide. The resulting "anions" or, correctly, 3-fluoro-1-azapentadienyl lithium compds. are conformationally mobile. While eight different coplanar structures are possible, one of them, a zigzag shaped (W) conformation must be largely favored. Depending on their nature, electrophiles attack the 1-azapentadienyl intermediates at either of the three nodal points: the nitrogen atom, the fluorine bearing a-position or the terminal g-position. Allyl type alkylating reagents produce a mixt. of a- and g-regioisomers from which the pure components can be sepd. Consecutive hydrolysis and redn. provides a-fluoroalkenals and a-fluoroallyl alcs. [on SciFinder (R)]

Official source

https://infoscience.epfl.ch/entities/publication/3f0fb8c4-dee6-4650-8774-1155c466cb25

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Manfred Schlosser
1994
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/3f0fb8c4-dee6-4650-8774-1155c466cb25

About this result

Related concepts (30)

Electrophile

In chemistry, an electrophile is a chemical species that forms bonds with nucleophiles by accepting an electron pair. Because electrophiles accept electrons, they are Lewis acids. Most electrophiles are positively charged, have an atom that carries a partial positive charge, or have an atom that does not have an octet of electrons. Electrophiles mainly interact with nucleophiles through addition and substitution reactions.

Organolithium reagent

In organometallic chemistry, organolithium reagents are chemical compounds that contain carbon–lithium (C–Li) bonds. These reagents are important in organic synthesis, and are frequently used to transfer the organic group or the lithium atom to the substrates in synthetic steps, through nucleophilic addition or simple deprotonation. Organolithium reagents are used in industry as an initiator for anionic polymerization, which leads to the production of various elastomers.

Alkene

In organic chemistry, an alkene is a hydrocarbon containing a carbon–carbon double bond. The double bond may be internal or in the terminal position. Terminal alkenes are also known as α-olefins. The International Union of Pure and Applied Chemistry (IUPAC) recommends using the name "alkene" only for acyclic hydrocarbons with just one double bond; alkadiene, alkatriene, etc., or polyene for acyclic hydrocarbons with two or more double bonds; cycloalkene, cycloalkadiene, etc.