A Versatile Bis-Allylboron Reagent for the Stereoselective Synthesis of Chiral Diols.
Angew Chem Int Ed Engl
; 57(43): 14276-14280, 2018 10 22.
Article
in En
| MEDLINE
| ID: mdl-30144261
ABSTRACT
Allylboron reagents are popular in synthesis owing to their versatility and the predictable stereochemical outcomes of their reactions with carbonyl compounds. Herein, we describe the synthesis of (Z,Z)-hexadienyl bis-boronate 1, a configurationally stable, crystalline, and easy to handle compound, which represents a class of bis-allylic boron reagents with heretofore untapped synthetic potential. In combination with a chiral phosphoric acid catalyst, the reagent can be employed for the enantioselective allyl transfer reaction to a variety of one-pot transformations, enabling swift access to functionalized 1,n-diols. The inâ
situ conversion of the reagent into the corresponding bis-borinic ester allows for the direct and diastereoselective two-fold allyl transfer to aldehydes. This affords C2 - or Ci -symmetric stereotetrads containing a 1,4-diol moiety for natural product synthesis. The usefulness of our method was demonstrated with a short synthesis of the lignan (±)-neo-olivil.
Key words
Full text:
1
Database:
MEDLINE
Main subject:
Boron Compounds
/
Indicators and Reagents
Type of study:
Prognostic_studies
Language:
En
Year:
2018
Type:
Article