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
收藏
页码：3233 / 3236
页数：4
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