Macrocyclische Imide: Vielseitige Synthese‐Bausteine bei Ringerweiterungsreaktionen | Zendy

Koch Thomas | Zendy; Hesse Manfred | Zendy

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Macrocyclische Imide: Vielseitige Synthese‐Bausteine bei Ringerweiterungsreaktionen

Author(s) -

Koch Thomas,

Hesse Manfred

Publication year - 1994

Publication title -

helvetica chimica acta

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.74

H-Index - 82

eISSN - 1522-2675

pISSN - 0018-019X

DOI - 10.1002/hlca.19940770321

Subject(s) - chemistry , synthon , nucleophile , imide , substituent , electrophile , ring (chemistry) , intramolecular force , stereochemistry , organic chemistry , catalysis

Macrocyclic Imides: Versatile Synthons in Ring‐Enlargement Reactions Macrocyclic imides differ from phthal‐ or succinimids in their increased electrophilicity. This property makes them versatile synthons for reactions with several nucleophiles. If a nucleophile is attached to the N ‐substituent of the imide, an intramolecular reaction will occur leading to ring‐enlarged products. Use of N, O, and C nucleophiles for this synthetic pathway is reported. Synthetic transformations of e.g. cyclododecanone leads to 17‐, 18‐, or 19‐membered macrolides, 11, 12, 15, 16, 21, 27, 30 , in three to five steps.

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