Selective Prins reaction of styrenes and formaldehyde catalyzed by 2,6-di-tert-butylphenoxy(difluoro)borane

被引：35

作者：

Bach, T ^{[1
]}

Löbel, J ^{[1
]}

机构：

[1] Tech Univ Munich, Lehrstuhl Organ Chem 1, D-85747 Garching, Germany

来源：

SYNTHESIS-STUTTGART | 2002年 / 17期

关键词：

carbocations; catalysis; chemoselectivity; electrophilic additions; Lewis acids;

D O I：

10.1055/s-2002-35645

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The sterically congested Lewis acid 1 was used as a catalyst in the Prins reaction of various styrenes and formaldehyde. 4-Aryl-1,3-dioxanes 5 were selectively formed as the exclusive products of the reaction with styrenes 4a-i and vinylthiophenes 4j-k. The reaction proceeded in most cases with good to excellent yields (55-99%). Styrenes which carried a strongly electron-withdrawing group (CN, CO2Me) did not react. The reaction with beta-alkylstyrenes 6 was successful for the methyl substituted substrate 6a and yielded (88%) trans-5-methyl-4-phenyl-1, 3-dioxane (7a) preferentially (dr = 75:25). For steric reasons, other beta-alkylstyrenes 6b-d did not react. The remarkable stereodiscrimination attained by catalyst 1 was employed in the regioselective transformation of 4-propenyl styrene (10) to dioxane 11 (83% yield).

引用

页码：2521 / 2526

页数：6

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