Journal
ORGANIC LETTERS
Volume 23, Issue 22, Pages 8738-8743Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c03190
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Funding
- Spanish Ministerio de Ciencia, Innovacion y Universidades (MCIU) [FEDER-PID2020-118422-GB-I00, FEDER-PID2019-109674-GB-I00]
- Basque Government [IT908-16]
- FPI fellowship
- Spanish MCIU
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Hydrazones derived from cycloalkenones undergo an enantioselective transannular formal (3 + 2) cycloaddition catalyzed by a chiral phosphoric acid, providing high yields and excellent stereocontrol in the formation of complex adducts. These adducts can be converted into versatile stereodefined decalin- or octahydro-1H-indene-derived 1,3-diamines through simple reductive N-N cleavage.
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 alpha-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.
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