2019
DOI: 10.1021/acs.joc.9b02491
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Synthesis of Fmoc-Protected Amino Alcohols via the Sharpless Asymmetric Aminohydroxylation Reaction Using FmocNHCl as the Nitrogen Source

Abstract: The aminohydroxylation of various alkenes using FmocNHCl as a nitrogen source is reported. In general, in the absence of a ligand, the reaction provided racemic Fmoc-protected amino alcohols with excellent regioselectivity but in low to moderate yields. However, in some instances, the yield of an amino alcohol product and the regioselectivity could be altered by the addition of a catalytic amount of triethylamine (TEA). The Sharpless asymmetric variant of this reaction (Sharpless asymmetric aminohydroxylation … Show more

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Cited by 5 publications
(5 citation statements)
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“…Fmoc- d - erythro -MeOAsp­( t -Bu)-OH was prepared using a route analogous to our previously disclosed routes (Scheme S1). …”
Section: Resultsmentioning
confidence: 99%
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“…Fmoc- d - erythro -MeOAsp­( t -Bu)-OH was prepared using a route analogous to our previously disclosed routes (Scheme S1). …”
Section: Resultsmentioning
confidence: 99%
“…Fmoc- d - threo -hAsn­(TBS)-OH was prepared using our procedure . A5D was prepared according to our procedure .…”
Section: Methodsmentioning
confidence: 99%
See 1 more Smart Citation
“…The route outlined in Scheme 3.10 was initially used and was based upon our synthesis of Fmoc-D-threo-HOAsn(Trt)-OH. 103,116 The route outlined in Scheme 3.13 was used for the large-scale synthesis of 3.9 which is based upon the procedures of Moeller et al 120 and Guzman-Martinez. 121 (50 mL), dried over MgSO4, evaporated and purified by FC (30 % EtOAc/70 % hexanes then 60 % EtOAc/38 % hexanes/2 % AcOH) to give 3.9 as an amorphous white solid (0.30 g, 60 % yield).…”
Section: Fmoc-d-erythro-hoasn(trt)-oh (39)mentioning
confidence: 99%
“…The next two residues, Fmoc-MeGlu­(O t Bu)-OH or Fmoc-Glu­(O t Bu)-OH, and Fmoc- d - e HOAsn­(Trt)-OH , were installed using DIC/HOBt to give peptides 17 and 18 . 2-Methylpiperidine (2-MP) was used to remove the Fmoc group to minimize the possibility of aminolysis of the ester bond.…”
mentioning
confidence: 99%