Synthesis of a 5-Hydroxypiperidine-2,3,4,6-tetramethanol, a New 2,6-Dideoxy-2,6-iminoheptitol Derivative

Jotterand, Nathalie; Vogel, Pierre

doi:10.1021/jo991228b

Cited by 12 publications

(1 citation statement)

References 28 publications

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“…Original 2,3,4,6-tetramethanol 5-hydroxypiperidine derivatives were prepared using the same chemistry. 35 The azido lactol reduction strategy has also been applied to generate the piperidine ring by formation of the C5-N bond. However, results reported by Fleet et al 36 and Effenberg 37 indicated that the reductive amination step occurs with a significant or complete loss of stereoselectivity.…”

Section: Reductive Aminationmentioning

confidence: 99%

Tactics and strategies for the synthesis of iminosugar C-glycosides: a review

Compain

Chagnault

Martin

2009

Tetrahedron: Asymmetry

158

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Section: Reductive Aminationmentioning

confidence: 99%

Tactics and strategies for the synthesis of iminosugar C-glycosides: a review

Compain

Chagnault

Martin

2009

Tetrahedron: Asymmetry

158

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Reductive Aminations of Carbonyl Compounds with Borohydride and Borane Reducing Agents

2002

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Reductive amination is an important tool for synthetic organic chemists in the construction of carbon‐nitrogen bonds. This reaction, also termed reductive alkylation, involves condensation of an aldehyde or ketone with an amine in the presence of a reducing agent. A wide variety of substrates can be used including aliphatic and aromatic aldehydes and ketones, and even benzophenones. A range of amines from ammonia to aromatic amines, including those with electron‐withdrawing substituents, can be employed. For particularly sluggish reactions, such as those involving weakly electrophilic carbonyl groups, poorly nucleophilic amines, or sterically congested reactive centers, additives such as molecular sieves or Lewis acids are often useful. This chapter focuses on those conditions in which the carbonyl component, amine, and reducing reagent react in the same vessel. This review is restricted to reductive aminations using borohydride and borane reducing agents. This chapter concentrates on reductive amination chemistry mediated by borohydride and other boron‐containing reducing agents from 1971, the year when sodium cyanoborohydride was introduced, through the middle of 1999. In addition to reductive aminations of aldehyde and ketone substrates, reactions of related structures including acetals, aminals, ketals, carboxylic acids, nitriles, and dicarbonyls that form a nitrogen‐containing ring are reviewed. Intramolecular processes in which the substrate contains both the carbonyl and amine moieties are described. The intramolecular variant is a useful method for preparing cyclic amines. All of the various boron‐containing hydride sources in reductive aminations, including labeled metal hydrides, are reviewed. Instances of reductive aminations that failed are described. Applications of this method to a solid support in parallel synthesis in combinatorial chemistry as well as reductive aminations that proceed in tandem with a second reaction such as reductive lactamizations are discussed.

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The Total Synthesis of C-Glycosides with Completely Resolved Seven-Carbon Backbone Polyol Stereochemistry: Stereochemical Correlations and Access toL-Configured and Other Rare Carbohydrates

et al. 2001

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The de novo synthesis of a full set of hydroxymethyl C-glycosides from only two precursors is described. The seven-carbon target molecules contain five stereocentres and bridge the stereochemical gap between natural D-configured and non-natural L-configured series of hexoses. Key steps include hydroxylation, differential protection, stereoselective reduction and desymmetrization of 8-oxabicyclo[3.2.1]oct-6-enes. C-Terminus differentiation and C-terminus excision of the seven-carbon polyol backbone lead to hexoses, including those of the L-series. A stereochemical and genetic classification of C-glycosides is presented.

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Synthesis of a 5-Hydroxypiperidine-2,3,4,6-tetramethanol, a New 2,6-Dideoxy-2,6-iminoheptitol Derivative

Cited by 12 publications

References 28 publications

Tactics and strategies for the synthesis of iminosugar C-glycosides: a review

Tactics and strategies for the synthesis of iminosugar C-glycosides: a review

Reductive Aminations of Carbonyl Compounds with Borohydride and Borane Reducing Agents

The Total Synthesis of C-Glycosides with Completely Resolved Seven-Carbon Backbone Polyol Stereochemistry: Stereochemical Correlations and Access toL-Configured and Other Rare Carbohydrates

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