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Transannular Enantioselective (3 + 2) Cycloaddition of Cycloalkenone Hydrazones under Bronsted Acid Catalysis.

ABSTRACT: Hydrazones derived from cycloalkenones undergo an enantioselective transannular formal (3 + 2) cycloaddition catalyzed by a chiral phosphoric acid. The reaction provides high yields and excellent stereocontrol in the formation of complex adducts with one or two α-tertiary amine moieties at the ring fusion, and these can be converted into very versatile stereodefined decalin- or octahydro-1H-indene-derived 1,3-diamines through simple reductive N-N cleavage.

SUBMITTER: Sendra J

PROVIDER: S-EPMC8609578 | biostudies-literature | 2021 Nov

REPOSITORIES: biostudies-literature

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Transannular Enantioselective (3 + 2) Cycloaddition of Cycloalkenone Hydrazones under Brønsted Acid Catalysis.

Sendra Jana J Reyes Efraim E Prieto Liher L Fernández Elena E Vicario Jose L JL

Organic letters 20211102 22

Hydrazones derived from cycloalkenones undergo an enantioselective transannular formal (3 + 2) cycloaddition catalyzed by a chiral phosphoric acid. The reaction provides high yields and excellent stereocontrol in the formation of complex adducts with one or two α-tertiary amine moieties at the ring fusion, and these can be converted into very versatile stereodefined decalin- or octahydro-1<i>H</i>-indene-derived 1,3-diamines through simple reductive N-N cleavage. ...[more]

PMID: 34726408

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