Remarkable rate acceleration of SmI3-mediated iodination of acetates of Baylis-Hillman adducts in ionic liquid: facile synthesis of (Z)-allyl iodides / 浙江大学学报(英文版)(B辑:生物医学和生物技术)
Journal of Zhejiang University. Science. B
;
(12): 193-197, 2006.
Article
in English
| WPRIM
| ID: wpr-263200
ABSTRACT
Stereoselective transformation of Baylis-Hillman acetates 1 into corresponding (Z)-allyl iodides 2 has been achieved by treatment of 1 with samarium triiodide in THF. Remarkable rate acceleration of samarium triiodide-mediated iodination of 1 was found when ionic liquid 1-n-butyl-3-methyl-imidazolium tetrafluroborate ([bmim]BF(4)) was used as reaction media in stead of THF. This novel approach proceeds readily at 50 degrees C within a few minutes to afford (Z)-allyl iodides 2 in excellent yields. A mechanism involving stereoselective iodination of the acetates of Baylis-Hillman adducts by samarium triiodide is described, in which a six-membered ring transition state played a key role in the stereoselective formation of 2.
Full text:
Available
Index:
WPRIM (Western Pacific)
Main subject:
Samarium
/
Solutions
/
Kinetics
/
Chemistry
/
Iodides
/
Ions
/
Acetates
Language:
English
Journal:
Journal of Zhejiang University. Science. B
Year:
2006
Type:
Article
Similar
MEDLINE
...
LILACS
LIS