Enantioselective Synthesis of 1,2-Dihydronaphthalene-1-carbaldehydes by Addition of Boronates to Isochromene Acetals Catalyzed by Tartaric Acid

被引：56

作者：

Luan, Yi ^{[1
]}

Barbato, Keith S. ^{[1
]}

Moquist, Philip N. ^{[1
]}

Kodama, Tomohiro ^{[1
]}

Schaus, Scott E. ^{[1
]}

机构：

[1] Boston Univ, Dept Chem, Boston, MA 02215 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2015年 / 137卷 / 09期

关键词：

DIELS-ALDER REACTIONS; CHIRAL NAPHTHYLOXAZOLINES; OXOCARBENIUM IONS; ASYMMETRIC ADDITIONS; STEREOSELECTIVITY; CYCLOADDITION; HYDROGENATION; ACCELERATION; NAPHTHALENES; DERIVATIVES;

D O I：

10.1021/jacs.5b00757

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Tartaric acid is an ideal asymmetric catalyst as it is abundant, cheap, and environmentally friendly. (+)-Tartaric acid was found to catalyze a novel enantioselective [4 + 2] cycloaddition of isochromene acetals and vinylboronates. A variety of substituted isochromene acetals were tolerated, furnishing the desired dihydronaphthalenes and dihydrobenzofluorene products in good yields. High enantiomeric ratios (up to 98.5:1.5) and excellent diastereoselectivities (all >99:1) were observed employing 10 mol % of (+)-tartaric acid as the catalyst, in combination with 5 mol % of Ho(OTf)(3).

引用

页码：3233 / 3236

页数：4

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