1980
DOI: 10.1002/anie.198001981
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Synthesis of Monosubstituted (S)‐Oxiranes in High Optical Purity

Abstract: rate with high vapor pressure at T>2500"C, thus accounting for their low content; the high melting impurities Ta and W, on the other hand, remain in the niobium. The samples R-Nb-1 were electrolyzed; the major impurities Ta and W are thus removed, but metals such as Cr, Fe, and Co are apparently involved by contamination. The samples R-Nb-2 were additionally zone refined and annealed, which leads to a marked decrease in the Cr, Fe, and Co content.The niobium thus obtained can be additionally characterized by i… Show more

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Cited by 25 publications
(6 citation statements)
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“…Hydrolysis reactions proceeded with very good yields (>84 %) for acetonides 15 , 17 and 21 (entries 1, 2 and 5). Substrates 19 and 20 , however, were transformed into their corresponding diols in slightly lower yields (79 % for 12 and 81 % for 13 ), probably due to the high volatility of the starting acetonides [25,26] . It should be noted that neither of them required any further purification step by chromatography.…”
Section: Resultsmentioning
confidence: 97%
See 1 more Smart Citation
“…Hydrolysis reactions proceeded with very good yields (>84 %) for acetonides 15 , 17 and 21 (entries 1, 2 and 5). Substrates 19 and 20 , however, were transformed into their corresponding diols in slightly lower yields (79 % for 12 and 81 % for 13 ), probably due to the high volatility of the starting acetonides [25,26] . It should be noted that neither of them required any further purification step by chromatography.…”
Section: Resultsmentioning
confidence: 97%
“…Substrates 19 and 20, however, were transformed into their corresponding diols in slightly lower yields (79 % for 12 and 81 % for 13), probably due to the high volatility of the starting acetonides. [25,26] It should be noted that neither of them required any further purification step by chromatography. In all cases, 1 H NMR spectra of the hydrolyzed compounds evidenced the absence of signals attributable to isopropylidene groups.…”
Section: Hydrolysis Of Acetonides Under Acid Catalysismentioning
confidence: 99%
“…Na etapa seguinte, o composto 3 foi reduzido com boroidreto de sódio conduzindo ao derivado acetonídeo hidroxilado 4. 20 O cetal cíclico 4 foi alquilado via derivado tosilato 5 através da reação com organocuprato e n-butil lítio, 20,21 obtendo-se o composto 6. Posteriormente, realizou-se a desproteção do cetal alquilado 6, com ácido clorídrico diluído.…”
Section: Resultsunclassified
“…Secondly, methyl 11( S )-jalapinolate [methyl 11( S )-hydroxyhexadecanoyl ester ( 25 )] was prepared employing a chiral pool approach starting from d -(+)-mannitol (Scheme ). 2( S )-Hydroxyheptanyl tosylate ( 14 ), readily obtained from d -mannitol in seven steps in a yield of 6.7% according to Barry's procedure, was treated with t -BuLi to afford the 1,2( S )-epoxyheptane ( 15 ) (overall yield of 4.7% from d -mannitol) . On the other hand, transformation of undecylenic acid to ω-bromononanyl ( tert -butyl dimethyl) silyl ether ( 21 ) was easily realized in six steps (overall 61% yield): reduction with LiAlH 4 , acetylation, oxidative cleavage of the double bond by KMnO 4 , Hunsdieck decarboxylic bromination, deacetylation, and protection of 1-OH with TBDMS.…”
Section: Resultsmentioning
confidence: 99%
“…The mixture was extracted with Et 2 O (70 mL × 3), washed with brine, dried over Na 2 SO 4 , and concentrated. Flash chromatography on a silica gel column (pentane−Et 2 O, 100:3) furnished a yellow oil 15 (1.429g, 70%): [α] 20 D −9.46 ( c 0.43, CHCl 3 ) (lit …”
Section: Methodsmentioning
confidence: 99%