Iron(III)‐BPsalan Complex Catalyzed Highly Enantioselective Dearomative Chlorination of 2‐Hydroxy‐1‐naphthoates

Abstract

A practical, efficient Fe(III)-BPsalan complex catalyzed asymmetric dearomative chlorination reaction of 2-hydroxy-1-naphthoates derivatives (22 examples) was developed. With readily available Fe(III)-BPsalan complex as catalyst at 5 mol% catalyst loading, various 2-hydroxy-1-naphthoates derivatives bearing different substituents were efficiently chlorinated to afford chiral naphthalenones bearing a Cl-containing all-substituted stereocenter in high yields and with good to excellent enantioselectivities under mild reaction conditions. The reaction could be conducted at gram scale with the high efficiency and selectivity retained. In addition, the reaction could be extended to asymmetric dearomative bromination to afford the corresponding brominated product in 87% yield and 76% ee.