4.8 Article

Asymmetric α-Functionalization of 2-Alkyl Azaarenes: Synthesis of Tertiary Fluorides Having Vicinal Stereogenic Centers

Journal

ORGANIC LETTERS
Volume 23, Issue 24, Pages 9441-9445

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c03626

Keywords

-

Funding

  1. SERB, India [SR/S2/JCB-17/2008]
  2. IIT Kanpur

Ask authors/readers for more resources

An enantioselective approach for synthesizing fluorinated azaarenes with vicinal quaternary-tertiary stereocenters has been summarized, utilizing a chiral copper(I)-phosphine complex to bind with the azaarenes followed by Michael addition to unsaturated acyl imidazoles, resulting in highly enantioselective compounds with excellent yields. Further functionalization of the acyl imidazole part has also been demonstrated.
An enantioselective approach for synthesizing fluorinated azaarenes containing vicinal quaternary-tertiary stereocenters is summarized. The chiral copper(I)-phosphine complex binds with the azaarenes followed by Michael addition to unsaturated acyl imidazoles, resulting in alpha-functionalized products with an excellent level of enantioselectivities (up to 99%), diastereoselectivities (>20:1), and yields (up to 97%). Furthermore, post-functionalization of the acyl imidazole part has also been demonstrated.

Authors

I am an author on this paper
Click your name to claim this paper and add it to your profile.

Reviews

Primary Rating

4.8
Not enough ratings

Secondary Ratings

Novelty
-
Significance
-
Scientific rigor
-
Rate this paper

Recommended

No Data Available
No Data Available