Cooperative Hydrogen-Bond-Donor Catalysis with Hydrogen Chloride Enables Highly Enantioselective Prins Cyclization Reactions.
J Am Chem Soc
; 143(48): 20077-20083, 2021 12 08.
Article
in En
| MEDLINE
| ID: mdl-34812618
ABSTRACT
Cooperative asymmetric catalysis with hydrogen chloride (HCl) and chiral dual-hydrogen-bond donors (HBDs) is applied successfully to highly enantioselective Prins cyclization reactions of a wide variety of simple alkenyl aldehydes. The optimal chiral catalysts were designed to withstand the strongly acidic reaction conditions and were found to induce rate accelerations of 2 orders of magnitude over reactions catalyzed by HCl alone. We propose that the combination of strong mineral acids and chiral hydrogen-bond-donor catalysts may represent a general strategy for inducing enantioselectivity in reactions that require highly acidic conditions.
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Main subject:
Alcohols
/
Aldehydes
/
Alkenes
/
Hydrochloric Acid
Language:
En
Journal:
J Am Chem Soc
Year:
2021
Document type:
Article
Affiliation country:
United States