The Preparation of 2-Methyloxazolidines and 2-Methyltetrahydro-1,3-oxazines from Acetylene and Aminoalcohols

Watanabe, Warren H.; Conlon, Lawrence E.

doi:10.1021/ja01568a043

Cited by 21 publications

(7 citation statements)

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“…The organic layers were combined, washed with saturated NaHCO 3 , dried with MgSO 4 , filtered, and concentrated. The crude conjugated cyclohexenol ester product was dissolved in 10 mL of CH 2 Cl 2 and cooled to −78 °C, and DBU (50 μL) was added …”

Section: Experimental Section3bmentioning

confidence: 99%

Lewis Acid-Promoted, Stereocontrolled, Gram Scale, Diels−Alder Cycloadditions of Electronically Matched 2-Pyrones and Vinyl Ethers: The Critical Importance of Molecular Sieves and the Temperature of Titanium Coordination with the Pyrone

et al. 1996

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(R)-(+)-Binol-titanium coordinates with commercial methyl 2-pyrone-3-carboxylate and promotes mild, highly enantiocontrolled Diels-Alder cycloadditions with electron-rich vinyl ether CH(2)=CHOCH(2)-1-naphthyl and vinyl silyl ether CH(2)=CHOSiMe(2)Bu-t leading to valuable 1alpha,25-dihydroxyvitamin D(3) (calcitriol) intermediate (-)-2. Unexpectedly, two subtle variables were found to be critical for obtaining reproducibly over 90% enantioselectivities in gram scale cycloadditions: (1) the moisture content (15-17% is best) of the molecular sieves used to prepare the binol-titanium complex according to the Mikami protocol and (2) the temperature (50 degrees C is best) at which the pyrone ester is mixed with the binol-titanium complex. Unsubstituted 2-pyrone undergoes ytterbium-promoted, high-pressure, regioselective, and stereoselective Diels-Alder cycloaddition with benzyl vinyl ether to form versatile bicyclic lactone (+/-)-4 on gram scale.

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Section: Experimental Section3bmentioning

confidence: 99%

Lewis Acid-Promoted, Stereocontrolled, Gram Scale, Diels−Alder Cycloadditions of Electronically Matched 2-Pyrones and Vinyl Ethers: The Critical Importance of Molecular Sieves and the Temperature of Titanium Coordination with the Pyrone

et al. 1996

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“…Four main synthetic pathways have been reported for the chemical modification of an alcohol with a functional vinyl ether: addition onto acetylene,62 phase transfer catalysis based on a Williamson reaction (between an alcoholate and 2‐chloroethyl vinyl ether),63–65 the modification of vinyl acetate in the presence of an iridium complex,66 and transetherification 63,67–72. This latter strategy has been extensively studied in the presence of either mercuric acetate or palladium acetate, especially by Watanabe and Conlon,67 Mc Keon,73 and Boutevin and Youssef 63. This last study even compared the transetherification with the Williamson reaction.…”

Section: Resultsmentioning

confidence: 99%

Organizations join forces to confront global cancer crisis

Printz¹

2011

Cancer

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The synthesis and characterization of novel poly(CTFE‐g‐oligoEO) graft copolymers [chlorotrifluoroethylene (CTFE) and ethylene oxide (EO)] are presented. First, vinyl ether monomers bearing oligo(EO) were prepared by transetherification of ω‐hydroxyoligo(EO) with ethyl vinyl ether catalyzed by a palladium complex in 70–84% yields. Two vinyl ethers of different molecular weights (three and 10 EO units) were thus obtained. Then, radical copolymerization of the above vinyl ethers with CTFE led to alternating poly(CTFE‐alt‐VE) copolymers that bore oligo(OE) side chains in satisfactory yields (65%). These original poly(CTFE‐g‐oligoEO) graft copolymers were characterized by 1H, 19F, and 13C NMR spectroscopy. Their molecular weights reached 19,000 g mol−1, and their thermal properties were investigated while their glass transition temperatures ranged between −42 and −36 °C. Their thermogravimetric analyses under air showed decomposition temperatures of 270 °C with 10% weight loss (Td,10%). These novel copolymers are of potential interest as polymer electrolytes in lithium ion batteries, showing room temperature conductivities ranging from 4.49 × 10−7 to 1.45 × 10−6 S cm−1 for unplasticized material. © 2012 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2013

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“…cis-and trans-propenyl tert-butyl ether (4c and 4t) were prepared by the alcohol exchange from propenyl ethyl ether (a mixture of 2c and 2t). 28 The yield of a mixture of 4c and 4t (~4:1) was about 20%, bp 101-102°(lit.29 4c, 101°).…”

Section: Methodsmentioning

confidence: 97%

Structure and reactivity of .alpha.,.beta.-unsaturated ethers. XV. Acid-Catalyzed hydrolysis of alkyl propenyl ethers. Relative cis/trans reactivity

Okuyama¹,

Fueno²

1974

J. Org. Chem.

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The Preparation of 2-Methyloxazolidines and 2-Methyltetrahydro-1,3-oxazines from Acetylene and Aminoalcohols

Cited by 21 publications

References 0 publications

Lewis Acid-Promoted, Stereocontrolled, Gram Scale, Diels−Alder Cycloadditions of Electronically Matched 2-Pyrones and Vinyl Ethers: The Critical Importance of Molecular Sieves and the Temperature of Titanium Coordination with the Pyrone

Lewis Acid-Promoted, Stereocontrolled, Gram Scale, Diels−Alder Cycloadditions of Electronically Matched 2-Pyrones and Vinyl Ethers: The Critical Importance of Molecular Sieves and the Temperature of Titanium Coordination with the Pyrone

Organizations join forces to confront global cancer crisis

Structure and reactivity of .alpha.,.beta.-unsaturated ethers. XV. Acid-Catalyzed hydrolysis of alkyl propenyl ethers. Relative cis/trans reactivity

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