Catalytic Enantioselective Synthesis of N–C Axially Chiral Mebroqualone and Its Derivatives through Reductive Asymmetric Desymmetrization

In the presence of (R)-DTBM-SEGPHOS-Pd­(OAc)2 catalyst, treatment of various 3-(2,6-dibromophenyl)­quinazolin-4-ones with NaBH4 gave optically active N–C axially chiral quinazolinone (mebroqualone) derivatives through reductive asymmetric desymmetrization (enantioselective monohydrodebromination) fo...

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Bibliographic Details
Published in:Organic letters 2016-11, Vol.18 (21), p.5700-5703
Main Authors: Hirai, Motohiro, Terada, Shumpei, Yoshida, Hiroaki, Ebine, Kenki, Hirata, Tomoaki, Kitagawa, Osamu
Format: Article
Language:English
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Summary:In the presence of (R)-DTBM-SEGPHOS-Pd­(OAc)2 catalyst, treatment of various 3-(2,6-dibromophenyl)­quinazolin-4-ones with NaBH4 gave optically active N–C axially chiral quinazolinone (mebroqualone) derivatives through reductive asymmetric desymmetrization (enantioselective monohydrodebromination) followed by kinetic resolution of the resulting monobromophenyl products (up to 99% ee). The enantioselectivity strongly depended on the substituent (R2) at the C4′position, amount of NaBH4, and reaction temperature.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.6b02865