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; Not stereoselective since reactions proceeds via planar carbocation. Finally, to further prove that this reaction can be accomplished on a preparative scale (0.5 mmol), we performed the asymmetric hydration of 1‐octene with Em‐OAH A248L under optimized conditions. The strict requirement for carboxylic acid substrates, however, limits the synthetic application of OAHs.27-32. Why doesn't a hydride shift occur? The final product is an alcohol. Propose the alkene that was the reactant for each of these products of oxymercuration. Various 1‐alkenes (C 5 –C 8 and C 10) were chosen for characterization of the different mutant enzymes with heptanoic acid as a decoy molecule. Such materials are peer reviewed and may be re‐organized for online delivery, but are not copy‐edited or typeset. Figure 3 shows the production of (S)‐2‐octanol with 50 % conversion, 22 % isolated yield and an enantiomeric excess of >99 % (Figure 3). The major product of the alkene hydration reaction is the Markovnikov product, resulting from the formation of a carbocation on the more highly substituted alkene carbon. Carotenoid‐1,2‐hydratases are specific to isoprene units in long‐chain terpenes12 and the linalool dehydratase isomerase is limited to isoprenoid dienes.20, 22 In contrast, fatty acid hydratases, including oleic acid hydratases (OAHs), convert isolated carbon–carbon double bonds of unsaturated fatty acids to the corresponding chiral alcohols. As 1‐octene is two carbon atoms shorter than 1‐decene, we assumed that 1‐octene might not bind effectively into the large substrate binding pocket of Em‐OAH. The functionalized alkenes 7‐bromohept‐1‐ene and 7‐octen‐1‐ol were converted with good activity and excellent enantioselectivity (>99 % ee, rows 1 and 2 in Figure 2 C and Figure S10). Moreover, we found that an equimolar ratio of 1‐decene and decoy molecule showed highest activity in 1‐decene hydration (Figure S5). A more detailed analysis of the Em‐OAH crystal structure (PDB code: 4UIR)32 further supports the functional relevance of position 248 for substrate binding as it is located at the end of the alkyl binding pocket and points towards the terminal carbon atom of the natural substrate oleic acid (Figure 2 A). Electrophilic hydration is the reverse dehydration of alcohols and has practical application in making alcohols for fuels and reagents for other reactions. Change ), You are commenting using your Facebook account. 1‐Decene was selected as a model substrate for the development of a selective hydration protocol. Water adds across the alkene's double bond in the hydration reaction. With the addition of water, alkynes can be hydrated to form enols that spontaneously tautomerize to ketones. The reaction is useful, however, because strong acids are not required, and carbocation rearrangements are avoided because no discreet carbocation intermediate forms. Carbon–carbon double bonds are one of the most important functional groups in organic chemistry and allow the synthesis of complex organic molecules. 3) (Hint: What is different about this problem?). identify the reagents, the alkyne, or both, needed to prepare a given ketone or a given cis alkene through a vinylic borane intermediate. Once the hydrogen is bound you have a carbocation, which gets attacked by the water molecule. There is a noticeable amount of side product that forms where the two methyl groups are, but the major product shown below is still the most significant due to the hyperconjugation that occurs by being in between the two cyclohexanes. if R & R’ in the third equation are not the same ) two isomeric ketones will be formed. ( Log Out / 

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