Synthesis of iminopolyols via Henry reaction: a short route to the α-manno- sidase inhibitor 1,4-dideoxy-1,4-imino-D-mannitol and to amino analogues†,1

Kieß, F.-M.; Poggendorf, P.; Jäger, Volker; Picasso, Sylviane

doi:10.1039/a706915d

Cited by 23 publications

(4 citation statements)

References 24 publications

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“…189 On the other hand the oxime can be oxidised with H 2 O 2 to nitroalkyl derivatives 153, which have been used as precursors for several azasugars 154 (Scheme 53). 190 The natural amino acid -quisqualic acid, as well as its -isomer, was synthesised from 8 via an oxime. A 17% overall yield was reported starting from N-Boc--serine (Scheme 54).…”

Section: Other Nucleophilic Additions; Formation Of Hydrazones Nitron...mentioning

confidence: 99%

Garner's aldehyde

Liang

Andersch

Bols

2001

J. Chem. Soc., Perkin Trans. 1

145

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Section: Other Nucleophilic Additions; Formation Of Hydrazones Nitron...mentioning

confidence: 99%

Garner's aldehyde

Liang

Andersch

Bols

2001

J. Chem. Soc., Perkin Trans. 1

145

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“…Polyhydroxylated pyrrolidines are known as potent glycosidase inhibitors and find useful therapeutic applications as antidiabetic, antiviral and anticancer drugs [85]. An interesting approach toward the preparation of dihydroxypyrrolidine 190 employs a nitroaldol reaction between 2-O-benzylglyceraldehyde 185 and optically active nitro derivative 186 (Scheme 46) [86]. The addition reaction is promoted by tetrabutylammonium fluoride and occurs with satisfactory diastereoselectivity leading to the Dmanno isomer 187 as main product.…”

Section: Pyrrolidinesmentioning

confidence: 99%

Nitroalkanes as Key Compounds for the Synthesis of Amino Derivatives

Ballini¹,

Gabrielli²,

Palmieri³

et al. 2011

COC

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The carbanion stabilizing effect of the nitro group makes nitroalkanes ideal reagents in carbon-carbon bond formation. Once introduced in a molecular framework, the nitro group is amenable to further transformations including reduction to primary amines. The aim of this review is to explore the utilization of nitroalkanes as effective substrates for the preparation of important target compounds featured by the amino group. These will include simple primary amines, diamines, amino acids, piperidines, pyrrolidines and heteroaromatic derivatives. A particular emphasis will be placed on the synthesis of enantioenriched amino derivatives mediated by organocatalysts or organometallic complexes.

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“…Okino et al used γ -lactam formed from the cyclization of the Michael adduct of diethylmalonate and β -nitrostyrene in the total synthesis of (R)-(-)-baclofen. 10 Versatile functionality of the nitro group provides easy transformations into amine, 11,12 ketone, 13,14 oxime, 15,16 or nitrile oxide 17 structures. In this manner, nitro functionality-bearing Michael adducts are potential starting materials for the synthesis of biologically active molecules containing γ -lactam cores.…”

Section: 9mentioning

confidence: 99%