Nickel-Catalyzed Asymmetric Addition of Aromatic Halides to Ketones: Highly Enantioselective Synthesis of Chiral 2,3-Dihydrobenzofurans Containing a Tertiary Alcohol

• Published in: Organic letters Vol. 22; no. 14; pp. 5353 - 5357
• Main Authors: Li, Ying, Li, Wendian, Tian, Jiangyan, Huang, Guozheng, Lv, Hui
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 17.07.2020; Amer Chemical Soc
• Subjects: alcohols; Chemistry; Chemistry, Organic; enantioselective synthesis; enantioselectivity; Physical Sciences; Science & Technology; ORGANOBORONIC ACIDS; FACILE SYNTHESIS; REAGENTS; ORGANOZINC ADDITIONS; ONE-POT; ARYLATION; ARYL IODIDES; ALDEHYDES; INTRAMOLECULAR NUCLEOPHILIC-ADDITION; ARYLBORONIC ACIDS
• ISSN: 1523-7060; 1523-7052; 1523-7052
• DOI: 10.1021/acs.orglett.0c01612

A highly enantioselective and straightforward synthetic procedure to chiral 3-hydroxy-2,3-dihydrobenzofurans has been developed by nickel/bisoxazoline-catalyzed intramolecular asymmetric addition of aryl halides to unactivated ketones, giving 2,3-dihydrobenzofurans with a chiral tertiary alcohol at the C-3 position in good yields and excellent enantioselectivities (up to 92% yield and 98% ee). The gram-scale reaction also proceeded smoothly without a loss of yield and enantioselectivity.