1982
DOI: 10.1021/jo00138a013
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Boron enolates in stereoselective syntheses of 2-enitols from O-benzyl aldoses by reaction with borohydride in 2-propanol. Configuration of E and Z enols from proton relaxation rates

Abstract: Isomerically pure E and Z forms of 2,4,6-tri-0-benzyl-2-dehydro-3-deoxy-D-eryt/iro-hex-2-enitol (4 and 3, respectively) were synthesized from 2,3,4,6-tetra-O-benzyl-D-glucopyranose by reactions employing sodium borohydride and 2-propanol under differing conditions. A cyclic boron enolate is proposed as a transition state to account for the formation of the Z olefin through regio-and stereoselective elimination, followed by hydride reduction. The elimination step was effected in the absence of boron to ensure g… Show more

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Cited by 9 publications
(8 citation statements)
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“…This is important in order to investigate the formation of the glycopolymer layer onto the gold NPs and the final properties of the resulting hybrid NP S , as compared with naked NPs, analyzing exclusively the influence of the glycopolymer layer rather than the shape or size of the particles. In addition, due to the partial decomposition of NaBH 4 in water at neutral pH, the further reduction of the glycopolymer dithiobenzoate end groups into thiols after the formation of the gold NPs may proceeds in mild conditions, limiting the possible degradation of the unprotected glucopyranose residues in strong reducing conditions …”
Section: Resultsmentioning
confidence: 99%
“…This is important in order to investigate the formation of the glycopolymer layer onto the gold NPs and the final properties of the resulting hybrid NP S , as compared with naked NPs, analyzing exclusively the influence of the glycopolymer layer rather than the shape or size of the particles. In addition, due to the partial decomposition of NaBH 4 in water at neutral pH, the further reduction of the glycopolymer dithiobenzoate end groups into thiols after the formation of the gold NPs may proceeds in mild conditions, limiting the possible degradation of the unprotected glucopyranose residues in strong reducing conditions …”
Section: Resultsmentioning
confidence: 99%
“…Nitroindole 9 (5 g, 11.8 mmol), CaCl2 (1.20 g, 10.8 mmol) and acid-washed zinc (30 g, 0.46 g-atom) were suspended in 250 mL of 95% ethanol. The mixture was refluxed for 2 h, cooled to room temperature, filtered, and evaporated to yield the aminoindole 10a: NMR (CDC13) 2.18 (d, J =1.2 Hz, 3 H), 4.93 (s, 2 ), 6.09 (d, J = 2.5 Hz, 1 H), 6.34 (d, J = 2.5 Hz, 1 H), 7.20-7.58 (m, 11 H); EIMS m/z 392,251,91 (100), 77. The amine was suspended in 100 mL of CH2C12, pyridine (1.02 g, 13.0 mmol) was added, and the mixture was cooled to 0 °C.…”
Section: Methodsmentioning
confidence: 99%
“…NMR (CDC13) 2.25 (s, 3 ), 2.80 (s, 3 H), 4.99 (s, 2 H), 6.40 (br s, 1 ), 6.61 (d, J = 1.5 Hz, 1 H), 6.88 (12b). N-Allylamide 10c (5.1 g, 10.8 mmol) and ammonium nitrate (861 mg, 10.8 mmol) were suspended in 20 mL of CH2C12.…”
Section: -(Benzyloxy)-3-methyl-l-(phenylsulfonyl)-5-[n-(2-mentioning
confidence: 99%
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