Highly Enantioselective Acylation of Acyclic Meso 1,3-Diols through Synergistic Isothiourea-Catalyzed Desymmetrization/Chiroablative Kinetic Resolution.
Org Lett
; 17(9): 2118-21, 2015 May 01.
Article
in En
| MEDLINE
| ID: mdl-25867851
ABSTRACT
A general and highly efficient organocatalyzed desymmetrization of acyclic meso 1,3-diols through acyl transfer using chiral isothioureas is described. The introduction of π-systems in the acyclic substrates provided new opportunities in terms of reactivity, enantioselectivity and synthetic potential. To reach this high level of enantioselectivity (up to er >991), the reaction proceeds through a synergistic mechanism involving a desymmetrization reaction and a chiroablative kinetic resolution process. This methodology was used with success as the sole enantioselective catalytic step (developed on a gram scale) to achieve the total synthesis of the antiosteoporotic diarylheptanoid (-)-diospongin A (7 steps).
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Main subject:
Thiourea
/
Diarylheptanoids
/
Alcohols
Language:
En
Journal:
Org Lett
Journal subject:
BIOQUIMICA
Year:
2015
Document type:
Article
Affiliation country:
France