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Allyl alcohol is converted mainly to glycidol, which is a chemical intermediate in the synthesis of glycerol, glycidyl ethers, esters, and amines. Also, a variety of polymerizable esters are prepared from allyl alcohol, e.g. diallyl phthalate. [5] Allyl alcohol has herbicidal activity and can be used as a weed eradicant [9]) and fungicide. [8]
The Krische allylation involves the enantioselective iridium-catalyzed addition of an allyl group to an aldehyde or an alcohol, resulting in the formation of a secondary homoallylic alcohol. [1] [2] The mechanism of the Krische allylation involves primary alcohol dehydrogenation or, when using aldehyde reactants, hydrogen transfer from 2 ...
Removal of a proton adjacent to the epoxide, elimination, and neutralization of the resulting alkoxide lead to synthetically useful allylic alcohol products. In reactions of chiral , non-racemic epoxides, the configuration of the allylic alcohol product matches that of the epoxide substrate at the carbon whose C–O bond does not break (the ...
The synthesis of allyl glycidyl ether by condensation of allyl alcohol and epichlorohydrin. AGE can also be synthesized by monoepoxidation of diallyl ether. [6] [7] The synthesis of allyl glycidyl ether by epoxidation of diallyl ether. Diepoxidation of the second alkene would produce diglycidyl ether. Allyl glycidyl ether is chiral.
When an α,β-unsaturated carbonyl is reduced, three products can result: an allyl alcohol from simple carbonyl reduction, a saturated ketone or aldehyde resulting from 1,4‑reduction (also called conjugate reduction), or the saturated alcohol from double reduction. [19]
Carbonyl allylation has been employed in the synthesis of polyketide natural products and other oxygenated molecules with a contiguous array of stereocenters. For example, allylstannanation of a threose-derived aldehyde affords the macrolide antascomicin B, which structurally resembles FK506 and rapamycin, and is a potent binder of FKBP12. [12]
In organic chemistry, an allyl group is a substituent with the structural formula −CH 2 −HC=CH 2. It consists of a methylene bridge ( −CH 2 − ) attached to a vinyl group ( −CH=CH 2 ). [ 1 ] [ 2 ] The name is derived from the scientific name for garlic , Allium sativum .
Isomers of BINOL. The Keck asymmetric allylation has many applications to the synthesis of natural products, [1] including (−)-Gloeosporone, [2] Epothilone A, [3] the CD-Subunit of spongistatins, [4] and the C10-C20 Subunit of rhizoxin A, [5] The Keck allylation has also been utilized to form substituted tetrahydropyrans enantioselectively, moieties found in products such as phorboxazole and ...