Enantioselective addition of arylboronic acids to methyl 2-formylbenzoates by using a ruthenium/Me-BIPAM catalyst for synthesis of chiral 3-aryl-isobenzofuranones

Masaaki Yohda; Yasunori Yamamoto

doi:10.1039/c5ob01661d

Enantioselective addition of arylboronic acids to methyl 2-formylbenzoates by using a ruthenium/Me-BIPAM catalyst for synthesis of chiral 3-aryl-isobenzofuranones

Org Biomol Chem. 2015 Nov 28;13(44):10874-80. doi: 10.1039/c5ob01661d. Epub 2015 Sep 14.

Authors

Masaaki Yohda¹, Yasunori Yamamoto

Affiliation

¹ Graduate School of Chemical Sciences and Engineering, Hokkaido University, Sapporo 060-8628, Japan.

PMID: 26366469
DOI: 10.1039/c5ob01661d

Abstract

Ruthenium/Me-BIPAM-catalyzed asymmetric addition of arylboronic acids to methyl 2-formylbenzoates afforded chiral 3-aryl-isobenzofuranones. [RuCl2(p-cymene)]2/Me-BIPAM and RuCl2(PPh3)3/Me-BIPAM catalyst systems tolerate a variety of functional groups and give high yields with high enantioselectivities.

MeSH terms

Benzoates / chemistry*
Boronic Acids / chemistry*
Catalysis
Cymenes
Furans / chemistry*
Methylation
Monoterpenes / chemistry
Ruthenium / chemistry*
Stereoisomerism

Substances

Benzoates
Boronic Acids
Cymenes
Furans
Monoterpenes
4-cymene
Ruthenium