Pd-Catalyzed Ligand-Directed Divergent Cycloaddition of Cyclic 1-Azadienes with Oxo-1,4-dipoles.
Org Lett
; 25(27): 5011-5016, 2023 Jul 14.
Article
em En
| MEDLINE
| ID: mdl-37382587
ABSTRACT
Ligand-directed divergent synthesis (LDS) is an important synthetic tool for the preparation of structurally diverse organic molecules without tedious steps to modify substrates. Herein, we introduce the realization of 3,4-, 1,2-, and 1,4-cyclization of benzo[d]isothiazole-1,1-dioxide-fused azadienes (BDAs) through LDS, leading to tetrahydro-2H-pyrans, oxazinanes, and tetrahydro-2H-1,5-oxazocines, respectively. Using phosphinooxazoline (PHOX) ligands, we have developed a [4 + 2] cycloaddition between BDAs and substituted 2-alkylidenetrimethylene carbonates, providing access to multi-substituted chiral tetrahydro-2H-pyrans in good yields with excellent enantio-, diastereo-, and regioselectivities.
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01-internacional
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MEDLINE
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Idioma:
En
Revista:
Org Lett
Assunto da revista:
BIOQUIMICA
Ano de publicação:
2023
Tipo de documento:
Article