The reactivity of the N-Boc protecting group: an underrated feature

Agami, Claude; Couty, François

doi:10.1016/s0040-4020(02)00131-x

Cited by 127 publications

(57 citation statements)

References 110 publications

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“…99 The reaction involves reduction of the aziridine aldehydes 184 with sodium borohydride followed by treatment with HCl in dioxane to furnish a single regioisomer of oxazolidinones 185 (Scheme 55). 16 The products were obtained in good yields with high enantiomeric excess with retention of configuration.…”

Section: Synthesis Of Oxazolidin-2-ones and Oxazolidine-2-thionesmentioning

confidence: 99%

Recent applications of aziridine ring expansion reactions in heterocyclic synthesis

Singh¹,

Sudheesh²,

Keroletswe³

2017

Arkivoc

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The inherent reactivity of the aziridine ring due to ring-strain makes it valuable building blocks for the synthesis of other heterocyclic motifs of biological relevance. Of particular significance is the generation of azomethine ylides from them and cycloaddition of ylides with alkenes, alkynes, and heterocumulenes. The ring undergoes opening followed by cyclization with a variety of reagents either in the presence of a catalyst or without any catalyst. This review article discusses the recent applications of aziridines in syntheses of four-to seven-membered heterocycles of biological relevance such as azetidines, 2

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Section: Synthesis Of Oxazolidin-2-ones and Oxazolidine-2-thionesmentioning

confidence: 99%

Recent applications of aziridine ring expansion reactions in heterocyclic synthesis

Singh¹,

Sudheesh²,

Keroletswe³

2017

Arkivoc

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“…Thus, when the methyl carbamate in 21 was replaced by a BOC group (substrate 26, [23] Scheme 6), a onepot decarboxylation/alkylation/cyclisation took place. The reaction intermediate 27 evolved by nucleophilic addition of the carbamate oxygen and concomitant loss of the tertbutyl group, [24] affording the spirocyclic carbamate 28 in 61 % global yield. The spirocyclic carbamates are structural analogues of spirocyclic lactams, and both kinds of compounds may be bioisosters.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Alkaloid Analogues from α‐Amino Acids by One‐Pot Radical Decarboxylation/Alkylation

et al. 2005

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“…It has been used in efficient syntheses of various heterocycles. 39 Diallyl pyrocarbonate introduces a common amino-protecting group, allyloxycarbonyl (Alloc), which can be removed selectively in the presence of other protecting groups (Scheme 34).…”

Section: Issn 1551-7012mentioning

confidence: 99%

Evolution of amide bond formation

Joullié¹,

Lassen²

2010

Arkivoc

158

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This paper is dedicated to Drs Bruce E. Maryanoff and Cynthia A. Maryanoff for their outstanding contribution to organic chemistry as industrial chemists AbstractThe presence of carboxamide groups is found in a large array of biologically important compounds. Peptides and proteins play an important role in modern biology. A key step in peptide production is the formation of the peptide bond, which involves amide bond formation. Chemical synthesis of large peptides by intermolecular coupling of smaller peptides using conventional peptide bond-forming techniques did not realize its potential advantages until recently. Using an approach based on highly specific and efficient chemical ligation of two peptide segments, the two subunits were ligated to form a new peptide bond. Native chemical ligation extended the concept by creating a native peptide bond and providing new approaches to protein engineering.

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The reactivity of the N-Boc protecting group: an underrated feature

Cited by 127 publications

References 110 publications

Recent applications of aziridine ring expansion reactions in heterocyclic synthesis

Recent applications of aziridine ring expansion reactions in heterocyclic synthesis

Synthesis of Alkaloid Analogues from α‐Amino Acids by One‐Pot Radical Decarboxylation/Alkylation

Evolution of amide bond formation

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