Catalytic Site-, Diastereo-, and Enantioselective Cascade Iodocyclization of 2-Geranylarenols.
Chem Asian J
; 18(7): e202300019, 2023 Apr 03.
Article
in En
| MEDLINE
| ID: mdl-36745467
ABSTRACT
A chiral amidophosphate-N-iodosuccinimide cooperative catalysis has been developed for the site-, diastereo-, and enantioselective iodocyclization of 2-geranylarenols with molecular iodine to give the corresponding iodo-containing polycyclic compounds with good levels of selectivity. This is the first example of a catalytic enantioselective iodocarbocyclization. A reactive chiral iodonium species is generated from molecular iodine via the dual halogen-bonding interactions with a chiral Lewis base and Lewis acid. The sterically demanding 3,3'-substituents of the chiral BINOL-derived amidophosphate are critical to induce the site-selective iodination at the less-hindered terminal alkenyl moiety of 2-geranylarenols.
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Language:
En
Journal:
Chem Asian J
Year:
2023
Document type:
Article
Affiliation country:
Japan