Cyclisierungsreaktionen β,γ‐ungesättigter Kohlensäurederivate. XI [1] Untersuchungen zur Stereochemie der Cyclofunktionalisierung β,γ‐ungesättigter Carbamidsäureester

Mühlstädt, M.; Meusinger, Reinhard; Olk, B.; Weber, Lutz; Widera, R.

doi:10.1002/prac.19863280302

Cited by 6 publications

(7 citation statements)

References 8 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Mp: 141.0-142.0 °C. [R]D 25 ) +26.7°(c 1.07, EtOAc). HRMS (m/z): calcd for C26H28NO3 [M + 1] + , 402.2069; found, 402.2079.…”

Section: Methodsmentioning

confidence: 99%

“…Mp: 182.5-183.5 °C. [R]D 25 ) +20.8°(c 1.01, EtOAc). 1 H NMR (CDCl3, 400 MHz; δ (ppm)): 7.60-7.18 (m, 15H), 7.42 (d, 6H, J ) 7.8 Hz), 7.29 (t, 6H, J ) 7.8 Hz), 7.21 (d, 3H, J ) 7.8 Hz), 5.25 (bs, 1H), 4.38 (m, 1H), 3.34 (m, 3H), 3.23 (dd, 1H, J ) 9.8, 5.9 Hz), 2.03 (dd, 1H, J ) 12.7, 2.9 Hz), 1.92 (m, 1H), 1.55 (bs, 1H).…”

Section: Methodsmentioning

confidence: 99%

“…A short synthesis for 1,3-oxazinan-2-ones was accomplished by reductive amination of 2-deoxy- d -ribose followed by cyclization of the aryl chloroformate derivatized amine . Other methods to synthesize 1,3-oxazinan-2-ones include halogen-mediated cyclization reactions, − a trans-sulfamoylation through sulfamide intermediates, selenium-mediated cyclization of amino alcohol with carbon monoxide, rearrangement from cyclic sulfates, intramolecular Michael additions, asymmetric dihydroxylation of homoallylic amines, and a Hoffmann rearrangement of a primary amide to form the carbamate . The iodoaminocyclization reaction is highly stereoselective when using a homoallyl carbamate with a chiral center at the homoallylic position (Scheme ) …”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

New Synthesis of Chiral 1,3-Oxazinan-2-ones from Carbohydrate Derivatives

2004

View full text Add to dashboard Cite

Chiral 1,3-oxazinan-2-ones are useful intermediates in synthesizing pharmaceutical compounds and amino alcohols. In this paper, we report a new synthetic method to chiral 6-hydroxymethyl 1,3-oxazinan-2-ones and their analogues from carbohydrate derivatives. The synthesis was accomplished by the reaction of optically pure 3-hydroxy-gamma-butyrolactone with a primary amine to give an amide, which was reduced and carbonylated to give the desired compound class.

show abstract

“…Mp: 141.0-142.0 °C. [R]D 25 ) +26.7°(c 1.07, EtOAc). HRMS (m/z): calcd for C26H28NO3 [M + 1] + , 402.2069; found, 402.2079.…”

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

New Synthesis of Chiral 1,3-Oxazinan-2-ones from Carbohydrate Derivatives

2004

View full text Add to dashboard Cite

show abstract

“…The methods for the synthesis of oxazinanones include the displacement of a carbamate such as benzyloxylcarbamate [60] or aryloxylcarbamate [61] with a hydroxyl group to give 1,3-oxazinan-2-one derivatives. Several other methods include halogen mediated cyclization reactions [62][63][64], reactions that involve sulfonamide or sulfate intermediates [65][66], selenium mediated cyclization of aminoalcohol with carbon monoxide [67], intramolecular Michael additions [68], asymmetric dihydroxylation of homoallylic amines [69], and a Hoffmann rearrangement reaction [70].…”

Section: Oxazinanone Synthesis and Characterizationmentioning

confidence: 99%

Synthesis and Antibacterial Properties of Oxazolidinones and Oxazinanones

Wang¹

2008

AIAMC

View full text Add to dashboard Cite

Oxazolidinones are important synthetic antibacterial agents useful for the treatment of multi antibiotic resistant Gram-positive bacterial infections. Since the launch of Linezolid, the first member of the oxazolidinone antibacterial family, there have been many studies directed towards structural optimization and the development of second generation oxazolidinones. The N-aryl 5-acetamido methyl oxazolidinone is the core structure for this class of antibacterial agents and the oxazolidinone component is essential for antibacterial activities. The chiral cyclic carbamate 5-hydroxymethyloxazolidin-2-one and 6-hydroxymethyl-[1,3]oxazinan-2-one are also important building blocks for synthesizing other biologically active compounds. Because of the importance of these compounds, many methods have been developed for their facile syntheses. In the first part of this paper, the synthesis of Linezolid and its analogs, as well as the preparation of the oxazolidinone core structures, will be reviewed. Secondly, recent developments in the area of oxazolidinone antibacterial agents including structure-activity relationships will be reviewed.

show abstract

“…The trans-relationship in carbamates 9 and 12 alone favours the five-membered-ring compound. Cyclisation of alkyl carbamates onto episulfonium, 12 episelenonium, 13,14 bromonium 12 and iodonium 13,14 ions also produce cyclic carbamates, but there is however no evidence in these cases that the cyclisations are reversible. The effect of changing the cyclohexane ring has not been investigated.…”

mentioning

confidence: 99%