New, Convenient Methods of Synthesis and Resolution of 1,2-Amino Alcohols

Periasamy, Muthu; Sivakumar, S.; Reddy, Meda Narsi

doi:10.1055/s-2003-41046

Cited by 11 publications

(7 citation statements)

References 6 publications

(6 reference statements)

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“…A method to access various racemic amino alcohol derivatives 30 has been developed in this laboratory by reduction of oxime esters using NaBH 4 /I 2 . [10] These aminoalcohols 30 are easily resolved using chiral dibenzoyl-l-tartaric acid to obtain partially resolved nonracemic samples. We have developed a conceptually new method for purification of the nonracemic amino alcohols to obtain samples of higher ee, through preparation of homochiral and heterochiral aggregates 31 using inexpensive achiral oxalic and fumaric acids (Scheme 3).…”

Section: Synthesis Of Chiral Amino Alcohols Through Resolution Of Rac...mentioning

confidence: 99%

Convenient Methods for the Synthesis of Chiral Amino Alcohols and Amines

Periasamy

Gurubrahamam²,

Sanjeevakumar³

et al. 2013

Chimia

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Section: Synthesis Of Chiral Amino Alcohols Through Resolution Of Rac...mentioning

confidence: 99%

Convenient Methods for the Synthesis of Chiral Amino Alcohols and Amines

Periasamy

Gurubrahamam²,

Sanjeevakumar³

et al. 2013

Chimia

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“…Then 1 was cyclized with thionyl chloride to obtain 4-methyl-1,2,3-thiadiazole-5-carboxylic acid ethyl ester 2. 15 Ester 2 was reduced by sodium borohydride in the presence of iodine to give 4-methyl-1,2,3-thiadiazole-5-methanol 3, 16 which was chlorinated by using thionyl chloride to obtain 5-chloromethyl-4-methyl-1,2,3-thiadiazole 4. The reaction of 4 with potassium phthalimide 5 gave intermediate N-substituted phthalimide which was subsequently treated with hydrazine to afford the corresponding aminomethyl compound 6 in one step.…”

Section: Synthesismentioning

confidence: 99%

“…The residue was purified by column chromatography over silica gel, elution with the cosolvents ethyl acetate-petroleum ether to obtain a colorless oil (1.20 g, 46% yield). 16 …”

Section: -Methyl-123-thiadiazole-5-methanol (3)mentioning

confidence: 99%

Synthesis, crystal structure, and herbicidal activity of novel 1,2,3-thiadiazole substituted 2-cyanoacrylates

Jian-Xin¹,

Wang²,

Bing³

et al. 2010

Arkivoc

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A series of novel 2-cyanoacrylates containing the 1,2,3-thiadiazole ring moiety were synthesized and characterized by 1 H NMR, 13C NMR, elemental analysis and, in one case, by X-ray crystallography. Most of these cyanoacrylates exhibited good herbicidal activities. In particular, (Z)-methoxyethyl-and (Z)-ethoxyethyl-2-cyano-3-isopropyl-3-(4-methyl-1,2,3-thiadiazol-5-yl)methylaminoacrylate 9h and 9g showed 100% herbicidal activities against rape and amaranth pigweed at a dose of 1.5 kg/ha. 2-Cyanoacrylates containing the thiadiazole ring are a new variation of this class of compound which still retain herbicidal activities.

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“…[5] Methods for the kinetic resolution of racemic 1 a to obtain enantiopure (R)-or (S)-1 a suffers from low theoretical yield (50%). [6] Enzyme catalysis is attractive due to high regio-and stereoselectivity, mild reaction conditions, and environmental friendliness. [7] However, the enzymatic approaches developed for the synthesis of (R)-and (S)-1 a also have drawbacks.…”

Section: Introductionmentioning

confidence: 99%

Bioproduction of Enantiopure (R)‐ and (S)‐2‐Phenylglycinols from Styrenes and Renewable Feedstocks

et al. 2020

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Enantiopure (R)-and (S)-2-phenylglycinols are important chiral building blocks for pharmaceutical manufacturing. Several chemical and enzymatic methods for their synthesis were reported, either involving multi-step synthesis or starting from a relatively complex chemical. Here, we developed one-pot simple syntheses of enantiopure (R)-and (S)-2-phenylglycinols from cheap starting materials and renewable feedstocks. Enzyme cascades consisting of epoxidation-hydrolysis-oxidation-transamination were developed to convert styrene 2 a to (R)-and (S)-2-phenylglycinol 1 a, with butanediol dehydrogenase for alcohol oxidation as well as BmTA and NfTA for (R)-and (S)-enantioselective transamination, respectively. The engineered E. coli strains expressing the cascades produced 1015 mg/L (R)-1 a in > 99% ee and 315 mg/L (S)-1 a in 91% ee, respectively, from styrene 2 a. The same cascade also converted substituted styrenes 2 b-k and indene 2 l into substituted (R)-phenylglycinols 1 b-k and (1R, 2R)-1-amino-2-indanol 1 l in 95-> 99% ee. To transform biobased L-phenylalanine 6 to (R)-1 a and (S)-1 a, (R)-and (S)-enantioselective enzyme cascades for deaminationdecarboxylation-epoxidation-hydrolysis-oxidation-transamination were developed. The engineered E. coli strains produced (R)-1 a and (S)-1 a in high ee at 576 mg/L and 356 mg/L, respectively, from L-phenylalanine 6, as the first synthesis of these compounds from a bio-based chemical. Finally, L-phenylalanine biosynthesis pathway was combined with (R)-or (S)-enantioselective cascade in one strain or coupled strains, to achieve the first synthesis of (R)-1 a and (S)-1 a from a renewable feedstock. The coupled strain approach enhanced the production, affording 274 and 384 mg/L (R)-1 a and 274 and 301 mg/L (S)-1 a, from glucose and glycerol, respectively. The developed methods could be potentially useful to produce these high-value chemicals from cheap starting materials and renewable feedstocks in a green and sustainable manner.

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New, Convenient Methods of Synthesis and Resolution of 1,2-Amino Alcohols

Cited by 11 publications

References 6 publications

Convenient Methods for the Synthesis of Chiral Amino Alcohols and Amines

Convenient Methods for the Synthesis of Chiral Amino Alcohols and Amines

Synthesis, crystal structure, and herbicidal activity of novel 1,2,3-thiadiazole substituted 2-cyanoacrylates

Bioproduction of Enantiopure (R)‐ and (S)‐2‐Phenylglycinols from Styrenes and Renewable Feedstocks

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