有機合成化学協会誌
Online ISSN : 1883-6526
Print ISSN : 0037-9980
総説および総合論文
キラルブレンステッド酸の開発と不斉合成反応への展開
秋山 隆彦
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ジャーナル 認証あり

2011 年 69 巻 8 号 p. 913-925

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We synthesized chiral phosphoric acids bearing 3,3'-substituents starting from (R)-BINOL and demonstrated their catalytic activity as chiral Brønsted acid. Proper choice of the 3,3'-substituents of the phosphoric acid is critical to attain excellent enantioselectivity. We wish to describe in this article the background of development of the catalyst, design of the catalyst, and application of them to a range of asymmetric reactions: (1) nucleophilic addition to aldimines, (2) cycloaddition toward aldimines, (3) Friedel-Crafts alkylation of indoles with nitroalkene, α,β-unsaturated ketone, and trifluoropyruvate, (4) kinetic resolution in the intramolecular aldol reaction, and (5) desymmetrization in the intramolecular aldol reaction. We also studied the role of the phosphoric acid and elucidated that phosphoryl oxygen played a critical role as a Lewis basic site.

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© 2011 社団法人 有機合成化学協会
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