CXLIII.—The influence of substituents on the formation and stability of heterocyclic compounds. Part I. Hydantoins

Ingold, C. K.; Sako, Shin-ichi; Thorpe, Jocelyn Field

doi:10.1039/ct9222101177

Cited by 58 publications

(31 citation statements)

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“…> 20:1; Table 1, entry 5). [22] The structurally related gem-disubstituted amide 1 g cyclised successfully under conditions A or B ( Table 2, entry 8). In CH 2 Cl 2 /NaHCO 3 , two separable products 4 g and 9 (overall yield 86 %) resulting from both N-and O-cyclisation were formed.…”

Section: Wwwchemeurjorgmentioning

confidence: 99%

Synthesis of 3‐Fluoropyrrolidines and 4‐Fluoropyrrolidin‐2‐ones from Allylic Fluorides

Combettes

Schuler

Patel

et al. 2012

Chemistry A European J

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Various 3-fluoropyrrolidines and 4-fluoropyrrolidin-2-ones were prepared by 5-exo-trig iodocyclisation from allylic fluorides bearing a pending nitrogen nucleophile. These bench-stable precursors were made accessible upon electrophilic fluorination of the corresponding allylsilanes. The presence of the allylic fluorine substituent induces syn-stereocontrol upon iodocyclisation with diastereomeric ratios ranging from 10:1 to > 20:1 for all N-tosyl-3-fluoropent-4-en-1-amines and amides. The sense and level of stereocontrol is strikingly similar to the corresponding iodocyclisation of structurally related allylic fluorides bearing pending oxygen nucleophiles. These results suggest that the syn selectivity observed upon ring closure involves I(2)-π complexes with the fluorine positioned inside.

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Section: Wwwchemeurjorgmentioning

confidence: 99%

Synthesis of 3‐Fluoropyrrolidines and 4‐Fluoropyrrolidin‐2‐ones from Allylic Fluorides

Combettes

Schuler

Patel

et al. 2012

Chemistry A European J

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“…During the past two decades several new synthetic approaches for the synthesis of cyclopropane amino acids have been reported 13, 14. One of the earliest and most straightforward synthetic methods used the alkylation of a glycine derivative or its congener with ethylene dibromide or its equivalent 19. Scheme depicts the first preparation of a cyclopropane amino acid.…”

Section: Cyclopropane Amino Acids15mentioning

confidence: 99%

Enantio‐ and diastereoselective syntheses of cyclic C^α‐tetrasubstituted α‐amino acids and their use to induce stable conformations in short peptides

Maity

König

2008

Biopolymers

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Cα‐Tetrasubstituted α‐amino acids are widely used to design and prepare peptides and peptide mimics with constrained conformations. Subcategories of these compounds are cyclic Cα‐tetrasubstituted α‐amino acids, in which both α‐substituents are covalently connected. This survey presents recent advances in the synthesis and application of cyclic Cα‐tetrasubstituted α‐amino acids in a systematic order beginning with cyclopropane amino acids, continuing with four, five, six membered rings, and ring structures larger than six‐membered. We discuss synthetic routes to the cyclic Cα‐tetrasubstituted α‐amino acids and their use as conformation determining elements in peptides. © 2007 Wiley Periodicals, Inc. Biopolymers (Pept Sci) 90: 8–27, 2008. This article was originally published online as an accepted preprint. The “Published Online” date corresponds to the preprint version. You can request a copy of the preprint by emailing the Biopolymers editorial office at biopolymers@wiley.com

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“…1-L2minocyclopropan-l-cnrbonsLure 3 ivurde erstmals 1922 von IXGOLD, SAKO und THORPE synthetisiert [4]. 1967 konnte BURROUGHTS die Aminosaure 3 aus Apfeln und Binien isolieren [5].…”

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A Facile Synthesis of 1‐Aminocyclopropane‐1‐carboxylic Acid

1990

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CXLIII.—The influence of substituents on the formation and stability of heterocyclic compounds. Part I. Hydantoins

Cited by 58 publications

References 0 publications

Synthesis of 3‐Fluoropyrrolidines and 4‐Fluoropyrrolidin‐2‐ones from Allylic Fluorides

Synthesis of 3‐Fluoropyrrolidines and 4‐Fluoropyrrolidin‐2‐ones from Allylic Fluorides

Enantio‐ and diastereoselective syntheses of cyclic C^α‐tetrasubstituted α‐amino acids and their use to induce stable conformations in short peptides

A Facile Synthesis of 1‐Aminocyclopropane‐1‐carboxylic Acid

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CXLIII.—The influence of substituents on the formation and stability of heterocyclic compounds. Part I. Hydantoins

Cited by 58 publications

References 0 publications

Synthesis of 3‐Fluoropyrrolidines and 4‐Fluoropyrrolidin‐2‐ones from Allylic Fluorides

Synthesis of 3‐Fluoropyrrolidines and 4‐Fluoropyrrolidin‐2‐ones from Allylic Fluorides

Enantio‐ and diastereoselective syntheses of cyclic Cα‐tetrasubstituted α‐amino acids and their use to induce stable conformations in short peptides

A Facile Synthesis of 1‐Aminocyclopropane‐1‐carboxylic Acid

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Enantio‐ and diastereoselective syntheses of cyclic C^α‐tetrasubstituted α‐amino acids and their use to induce stable conformations in short peptides