Absolute configuration of glycerol derivatives. 3. Synthesis and Cupra A circular dichroism spectra of some chiral 3-aryloxy-1,2-propanediols and 3-aryloxy-1-amino-2-propanols

Wl, Nelson; Je, Wennerstrom; Sankar,

doi:10.1021/jo00426a016

Cited by 77 publications

(21 citation statements)

References 23 publications

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“…The solution was extracted with diethyl ether, the organic phase was washed with brine, and pure compound 27 [41] was obtained after evaporation of the solvent.…”

mentioning

confidence: 99%

Ring‐Closure Reactions through Intramolecular Displacement of the Phenylselenonyl Group by Nitrogen Nucleophiles: A New Stereospecific Synthesis of N‐Tosyl and N‐Benzoyl‐1,3‐oxazolidin‐2‐ones from β‐Hydroxyalkyl Phenyl Selenides

Tiecco

Testaferri

Temperini

et al. 2004

Chemistry A European J

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A new and convenient method for the stereospecific synthesis of variously substituted 1,3-oxazolidin-2-ones from the easily available beta-hydroxyalkyl phenyl selenides is presented. After transformation into the N-tosyl or N-benzoyl carbamates, the selenides were oxidized to the corresponding selenones. The key step of the process is the ring-closure reaction, which occurs by stereospecific intramolecular nucleophilic substitution of the selenone group by the nitrogen atom of the carbamate. Enantiomerically pure 1,3-oxazolidin-2-one derivatives can be easily prepared by using enantiomerically pure beta-hydroxyalkyl phenyl selenides as starting materials.

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“…The solution was extracted with diethyl ether, the organic phase was washed with brine, and pure compound 27 [41] was obtained after evaporation of the solvent.…”

mentioning

confidence: 99%

Ring‐Closure Reactions through Intramolecular Displacement of the Phenylselenonyl Group by Nitrogen Nucleophiles: A New Stereospecific Synthesis of N‐Tosyl and N‐Benzoyl‐1,3‐oxazolidin‐2‐ones from β‐Hydroxyalkyl Phenyl Selenides

Tiecco

Testaferri

Temperini

et al. 2004

Chemistry A European J

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“…4 ) These conversions elucidated at the same time that the absolute configuration of ( -)-1 was assigned to (S). Accordingly, the lipase preferentially hydrolyzed the (R)-isomer of (± )-1 to leave the (S)-isomer.…”

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confidence: 84%

“…I: 4. (4). A mixture of (S)-1 ([lXjo -5.2°, 1.03g, 5.28 mmol), 2-allyloxyphenol (446 mg, 2.9 mmol) and calcium hydroxide (976 mg, 13 mmol) in water (20ml) was stirred at 50 ~ 60°C for 2 hr under an argon atmosphere.…”

Section: B) Preparation Of a Mixture Of (R)-2-acetoxy-3-chloroi-propamentioning

confidence: 99%

“…7 ) (S)-and (R)-Oxprenolol [1-(2-allyloxyphenoxy)-3-isopropylamino-2-propanol] were synthesized from (S)-and (R)-3-tosyloxy-I,2-propanediol acetonide, respectively, which were derived from D-mannitol by many steps. 3,4) Thus, by the use of (S)-dioI5 newly prepared from (S)-I, we successfully achieved the synthesis of optically pure (S)-propranolol (9): Recrystallization of (S)-5 of [oc]o +7.15° from ethyl acetate-acetic acid (95: 5) gave almost optically pure (S)-5 of [oc]o + 7.7°. This diol was allowed to react with 30% hydrogen.…”

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confidence: 99%

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Asymmetric Hydrolysis of (±)-1,2-Diacetoxy-3-chloropropane and Its Related Compounds with Lipase. Synthesis of Optically Pure (S)-Propranolol

Iriuchijima¹,

Kojima²

1982

Agricultural and Biological Chemistry

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Asymmetric hydrolysis of (± )-1,2-diacetoxy-3-chloropropane (1) with a very small amount of a lipoprotein lipase gave (S)-1 of90% enantiomeric excess (e.e.). Reactions of (S)-1 with phenols in an alkaline condition yielded the corresponding (S)-3-aryloxy-I,2-propanediols. From (S)-3-(1-naphthoxy)-1,2-propanediol (5) was synthesized the optically pure (S)-isomer of propranolol [1-isopropylamino-3-(I-naphthoxy)-2-propanoll (9), one of the p-adrenergic blocking agents. Hydrolysis of (±)-1,2-diacetoxy-3-bromopropane (11) and (±)-1,2-diacetoxyethylbenzene (12) with the lipase afforded (S)-11 of 77% e.e. and (R)-12 of 73% e.e., respectively.

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“…The resulting amine 5a exhibited specific rotation of [a]~l -4.7°(c=0.6, CHCI 3 ), suggesting that the absolute configuration is 8,8) being the same as that of physiologically active fJ-blockers. As shown in Table III, chiral acetates 4b and 4c also gave the corresponding amines 5b and 5c, respectively, according to the same procedures.…”

Section: Received March 24 1986mentioning

confidence: 99%

Asymmetric Hydrolysis of Aryloxy-acetaldehyde Cyanohydrin Acetates

Ohta

Miyamae

Tsuchihashi

1986

Agricultural and Biological Chemistry

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Absolute configuration of glycerol derivatives. 3. Synthesis and Cupra A circular dichroism spectra of some chiral 3-aryloxy-1,2-propanediols and 3-aryloxy-1-amino-2-propanols

Abstract: Aus dem Isopropyliden‐glycerin (I) entsteht ein Tosylat (II) sowie über (III) und (IV) das stereoisomere Tosylat (V).

Cited by 77 publications

References 23 publications

Ring‐Closure Reactions through Intramolecular Displacement of the Phenylselenonyl Group by Nitrogen Nucleophiles: A New Stereospecific Synthesis of N‐Tosyl and N‐Benzoyl‐1,3‐oxazolidin‐2‐ones from β‐Hydroxyalkyl Phenyl Selenides

Ring‐Closure Reactions through Intramolecular Displacement of the Phenylselenonyl Group by Nitrogen Nucleophiles: A New Stereospecific Synthesis of N‐Tosyl and N‐Benzoyl‐1,3‐oxazolidin‐2‐ones from β‐Hydroxyalkyl Phenyl Selenides

Asymmetric Hydrolysis of (±)-1,2-Diacetoxy-3-chloropropane and Its Related Compounds with Lipase. Synthesis of Optically Pure (S)-Propranolol

Asymmetric Hydrolysis of Aryloxy-acetaldehyde Cyanohydrin Acetates

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