The Chemistry of α,β-Unsaturated Ethers. III. Self Condensation<sup>1</sup>

Hoaglin, R. I.; Kubler, D. G.; Montagna, A. E.

doi:10.1021/ja01553a036

Cited by 15 publications

(2 citation statements)

References 2 publications

(2 reference statements)

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“…A similar dimerization of vinyl ethers to acetals by Hg(OAc) 2 /BF 3 ·Et 2 O has been reported . This system produces a significant amount of trimer, tetramer, and polymer side products and also dimerizes substituted vinyl ethers such as EtCHCHOEt and CH 2 CMeOEt.…”

supporting

confidence: 62%

Palladium-Catalyzed Dimerization of Vinyl Ethers to Acetals

Chen

Jordan

2010

J. Am. Chem. Soc.

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(Alpha-diimine)PdCl(+) species catalytically dimerize alkyl and silyl vinyl ethers to beta,gamma-unsaturated CH(2)=CHCH(2)CH(OR)(2) acetals, and they cyclize divinyl ethers to analogous cyclic acetals. A plausible mechanism comprises in situ generation of an active PdOR alkoxide species, double vinyl ether insertion to generate Pd{CH(2)CH(OR)CH(2)CH(OR)(2)} species, and beta-OR elimination to generate the acetal product. In the presence of vinyl ethers, (alpha-diimine)PdCl(+) species can be used to initiate ethylene polymerization.

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supporting

confidence: 62%

Palladium-Catalyzed Dimerization of Vinyl Ethers to Acetals

Chen

Jordan

2010

J. Am. Chem. Soc.

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“…Nitroaldehyde (±)‐ 6 was obtained starting from aldehyde 8 , as reported by El Blidi et al 16b. Finally, aldehyde 8 was prepared by ozonolysis of the corresponding alkene,25 previously obtained using the procedure of Hoaglin et al 26…”

Section: Methodsmentioning

confidence: 99%

L‐Rhamnulose‐1‐phosphate Aldolase from Thermotoga maritima in Organic Synthesis: One‐Pot Multistep Reactions for the Preparation of Imino‐ and Nitrocyclitols

et al. 2015

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Abstract. Rhamnulose-1-phosphate aldolase from Thermotoga maritima (Rhu1PATm) has been recently cloned and characterized. This hyperthermophilic enzyme offers intriguing possibilities for practical catalysis. This is due to its high stability under extreme reaction conditions, such as high temperature or the presence of organic co-solvents. The Rhu1PATm potentiality in organic synthesis has been explored focusing on i) the reaction stereocontrol, ii) the possibility of combining it with other mesophilic enzymes in multienzyme systems and iii) its application to the synthesis of imino-and nitrocyclitols. In our study, Rhu1PATm diastereoselectivity was similar to the one reported by Rhu1PA from Escherichia coli (Rhu1PAEc). However, we observed significant differences for some aldehyde acceptors. Indeed, the diastereoselectivity control was not complete, since mixtures of L-threo (2R,3S; natural stereopreference) and D-erythro (2R,3R) diastereoisomers were obtained as described for Rhu1PAEc. Rhu1PATm was able to catalyse aldol reactions using nitroaldehydes and N-Cbzaminoaldehydes. Conversion of the selected nitroaldehydes was complete, leading to mixtures of L-threo and D-erythro diastereoisomers, in 95:5 and 75:25 ratios. When N-Cbz-aminoaldehydes were used, aldol reaction yields were lower and the stereoselectivity L-threo:D-erythro ranged between 32:68 to >95:5.

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Acetylene‐Derived Chemicals

Hort

Taylor

2000

Kirk-Othmer Encyclopedia of Chemical Technology

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Acetylene, C 2 H 2 , is an extremely reactive hydrocarbon, principally used as a chemical intermediate. Because of its relatively high price, there have been continuing successful efforts to replace acetylene with cheaper raw materials. The name ethynylation was coined by Reppe to describe the addition of acetylene to carbonyl compounds. Principal Reppe acetylene chemicals include propargyl alcohol, butynediol, butenediol, butanediol, and butyrolactone. Butynediol is principally consumed in manufacture of butenediol and butanediol. Butanediol is consumed in manufacture of butyrolactone and tetrahydrofuran. Large amounts are also used as a monomer for polyesters and polyurethanes. Butyrolactone is principally used as an intermediate for manufacture of pyrrolidones. Propargyl alcohol is a primary skin irritant and severe eye irritant, highly toxic by all means of ingestion. Catalytic vinylation, in which a labile hydrogen compound adds to acetylene, forming a double bond, has been applied to a wide range of alcohols, phenols, thiols, and carboxylic acids. Vinyl ethers are used in the manufacture of glutaraldehyde and as monomers.

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The Chemistry of α,β-Unsaturated Ethers. III. Self Condensation¹

Cited by 15 publications

References 2 publications

Palladium-Catalyzed Dimerization of Vinyl Ethers to Acetals

Palladium-Catalyzed Dimerization of Vinyl Ethers to Acetals

L‐Rhamnulose‐1‐phosphate Aldolase from Thermotoga maritima in Organic Synthesis: One‐Pot Multistep Reactions for the Preparation of Imino‐ and Nitrocyclitols

Acetylene‐Derived Chemicals

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The Chemistry of α,β-Unsaturated Ethers. III. Self Condensation1

Cited by 15 publications

References 2 publications

Palladium-Catalyzed Dimerization of Vinyl Ethers to Acetals

Palladium-Catalyzed Dimerization of Vinyl Ethers to Acetals

L‐Rhamnulose‐1‐phosphate Aldolase from Thermotoga maritima in Organic Synthesis: One‐Pot Multistep Reactions for the Preparation of Imino‐ and Nitrocyclitols

Acetylene‐Derived Chemicals

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The Chemistry of α,β-Unsaturated Ethers. III. Self Condensation¹