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Highly Selective Synthesis of Seven-Membered Azaspiro Compounds by a Rh(I)-Catalyzed Cycloisomerization/Diels-Alder Cascade of 1,5-Bisallenes.

ABSTRACT: The synthesis of spiro compounds featuring seven- and six-membered rings in the spirobicyclic motif is successfully achieved through a cascade process encompassing a rhodium(I)-catalyzed cycloisomerization followed by a highly selective Diels-Alder homodimerization. The scope of the reaction is analyzed based on a series of synthetic substrates, and control experiments and DFT calculations led us to justify the exquisite degree of selectivity observed.

SUBMITTER: Vila J

PROVIDER: S-EPMC9016767 | biostudies-literature | 2022 Apr

REPOSITORIES: biostudies-literature

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Highly Selective Synthesis of Seven-Membered Azaspiro Compounds by a Rh(I)-Catalyzed Cycloisomerization/Diels-Alder Cascade of 1,5-Bisallenes.

Vila Jordi J Solà Miquel M Pla-Quintana Anna A Roglans Anna A

The Journal of organic chemistry 20220324 8

The synthesis of spiro compounds featuring seven- and six-membered rings in the spirobicyclic motif is successfully achieved through a cascade process encompassing a rhodium(I)-catalyzed cycloisomerization followed by a highly selective Diels-Alder homodimerization. The scope of the reaction is analyzed based on a series of synthetic substrates, and control experiments and DFT calculations led us to justify the exquisite degree of selectivity observed. ...[more]

PMID: 35324177

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