Highly Efficient Kinetic Resolution of PHANOL by Chiral Phosphoric Acid Catalyzed Asymmetric Acylation

被引：8

作者：

Mori, Keiji ^{[1
,2
]}

Kishi, Hiroki ^{[1
]}

Akiyama, Takahiko ^{[1
]}

机构：

[1] Gakushuin Univ, Fac Sci, Dept Chem, Toshima Ku, 1-5-1 Mejiro, Tokyo 1718588, Japan

[2] Tokyo Univ Agr & Technol, Fac Sci, Dept Appl Chem, 2-24-16 Nakacho, Koganei, Tokyo 1848588, Japan

来源：

SYNTHESIS-STUTTGART | 2017年 / 49卷 / 02期

关键词：

asymmetric synthesis; chiral biaryl; asymmetric acylation; kinetic resolution; chiral phosphoric acid; STRONGER BRONSTED ACIDS; BOND-FORMING REACTIONS; MACRO RINGS; RECENT PROGRESS; ELECTROPHILIC SUBSTITUTION; SECONDARY ALCOHOLS; LIGANDS; HYDROXYCARBONYLATION; INTERCONVERSIONS; ORGANOCATALYSTS;

D O I：

10.1055/s-0036-1588898

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report herein a highly efficient kinetic resolution of PHANOL by chiral phosphoric acid catalyzed asymmetric acylation. PHANOL enantiomers were well differentiated by the chiral environment of chiral phosphoric acid, and both the corresponding monoester and PHANOL were obtained with excellent enantioselectivities (98% ee and 92% ee, respectively). Detailed examination of the substrates suggests that the presence of two hydroxy groups in PHANOL was critical for both reactivity and enantioselectivity.

引用

页码：365 / 370

页数：6

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