Straightforward Synthetic Approach to Aminoalcohols with 9-oxabicyclo[3.3.1]nonane or Cyclooctane Core via Nucleophilic Ring-Opening of Spirocyclic Bis(oxiranes).

Olga V Ryzhikova, Daiana V Savchenkova, Sergey V Kositov, Yuri K Grishin, Olga A Maloshitskaya, Kseniya N Sedenkova, Elena B Averina

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Article in Molecules (Basel, Switzerland), 2026. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.

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7 authors.

Olga V RyzhikovaDepartment of Chemistry, Lomonosov Moscow State University, Leninskie Gory 1-3, 119991 Moscow, Russia.

Daiana V SavchenkovaDepartment of Chemistry, Lomonosov Moscow State University, Leninskie Gory 1-3, 119991 Moscow, Russia.

Sergey V KositovDepartment of Chemistry, Lomonosov Moscow State University, Leninskie Gory 1-3, 119991 Moscow, Russia.

Yuri K GrishinDepartment of Chemistry, Lomonosov Moscow State University, Leninskie Gory 1-3, 119991 Moscow, Russia.ORCID 0000-0001-7709-5245

Olga A MaloshitskayaDepartment of Chemistry, Lomonosov Moscow State University, Leninskie Gory 1-3, 119991 Moscow, Russia.ORCID 0000-0002-3579-8863

Kseniya N SedenkovaDepartment of Chemistry, Lomonosov Moscow State University, Leninskie Gory 1-3, 119991 Moscow, Russia.ORCID 0000-0002-0294-9581

Elena B AverinaDepartment of Chemistry, Lomonosov Moscow State University, Leninskie Gory 1-3, 119991 Moscow, Russia.ORCID 0000-0002-6107-2003

Funding

State Assignment 121021000105-7

6 · The paper itself

Abstract

Nucleophilic ring-opening of bis(oxiranes), containing several reactive centers, can be used to elaborate straightforward atom-economy and stereoselective approaches to polyfunctionalized compounds. In the present work, ring-opening of cis- and trans-diastereomers of a spirocyclic bis(oxirane), containing a cyclooctane core (namely, 1,8-dioxadispiro[2.3.2.3]dodecane), upon treatment with various amines, was studied. Trans-isomer afforded aminoalcohols with 9-oxabicyclo[3.3.1]nonane moiety, formed via domino-process, including opening of an oxirane ring followed by intramolecular cyclization. Ring-opening of cis-isomer gave aminosubstituted cis-cyclooctane-1,5-diols, derived from independent reaction of two oxirane moieties. Activation of oxirane rings by the addition of LiClO

Indexed as

9-oxabicyclo[3.3.1]nonanesaminesaminodiolscyclooctanesdomino reactionintramolecular cyclizationoxiranesring-opening

Identifiers

PMID41599302

DOI10.3390/molecules31020252

PMCPMC12843951

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