Asymmetric Synthesis of Hydrodibenzofurans from Norcaradienes: Kinetic Resolution via [3 + 2] Cycloaddition with Quinones.
Org Lett
; 26(18): 3844-3849, 2024 May 10.
Article
em En
| MEDLINE
| ID: mdl-38662793
ABSTRACT
The catalytic asymmetric [3 + 2] cycloaddition of racemic norcaradienes with quinones to construct multicyclic hydrodibenzofurans was achieved by the use of chiral N,N'-dioxide/metal complex catalysts. Kinetic resolution of norcaradienes accompanied by partial racemization occurred, and one enantiomer in prior acted as the C2 synthon to participate in diastereoselective cycloaddition. An enantiodivergent synthesis via a switch of metal ions was observed when naphthoquinone was used as the partner. DFT calculations revealed the profiles of the cycloaddition processes.
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Coleções:
01-internacional
Base de dados:
MEDLINE
Idioma:
En
Revista:
Org Lett
Ano de publicação:
2024
Tipo de documento:
Article