Regioselective asymmetric aminohydroxylation of precursors to 2,3,6-trideoxy-3-aminohexoses

Davey, Roger M.; Brimble, Margaret A.; McLeod, Malcolm D.

doi:10.1016/s0040-4039(00)00798-x

Cited by 16 publications

(6 citation statements)

References 26 publications

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“…In a study directed towards the synthesis of amino sugars, engineering of AA substrate 97a allowed improvement of what was initially poor regioselectivity favouring the undesired α-amino isomer 98a (Scheme 28). 77 Replacement of the dimethyl acetal of 97a with methyl substituents to give substrate 97b resulted in reversal of regioselectivity to favour the desired regioisomer 99b in moderate ee. The selectivity was greatly enhanced upon substitution of the alkyl chain with an aromatic ether to give substrate 97c.…”

Section: Synthetic Applicationsmentioning

confidence: 99%

The Sharpless asymmetric aminohydroxylation

Bodkin

McLeod

2002

J. Chem. Soc., Perkin Trans. 1

190

116

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Section: Synthetic Applicationsmentioning

confidence: 99%

The Sharpless asymmetric aminohydroxylation

Bodkin

McLeod

2002

J. Chem. Soc., Perkin Trans. 1

190

116

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“…Scheme 1). [23] In that context, the PHAL ligand 28 immobilized to an organic copolymer has been successfully prepared (Figure 1), demonstrating the AA with a heterogeneous catalyst. [24] Selectivities up to 87% were achieved in the AA of isopropyl trans-cinnamate, compared to 96% ee with the corresponding non immobilized ligand.…”

Section: Reagents and Catalysts 4 New Ligands And Catalystsmentioning

confidence: 99%

The Sharpless Asymmetric Aminohydroxylation -Scope and Limitation

Nilov

Reiser

2002

Advanced Synthesis & Catalysis

113

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The asymmetric aminohydroxylation (AA) has emerged as a valuable tool in organic synthesis. Recent developments, such as ligandless variants, new nitrogen reagents and new substrates have considerably broadened the utility of the process. Nevertheless, the understanding of the AA, both in terms of mechanism as well as applicability to common synthetic tasks is still limited. This article summarizes the scope and limitation of the AA with special emphasis on recent advances.

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“…[23] In that context, the PHAL ligand 28 immobilized to an organic copolymer has been successfully prepared (Figure 1), demonstrating the AA with a heterogeneous catalyst. Scheme 1).…”

Section: Reagents and Catalysts 4 New Ligands And Catalystsmentioning

confidence: 94%