A combination of directing groups and chiral anion phase-transfer catalysis for enantioselective fluorination of alkenes

被引：96

作者：

Wu, Jeffrey ^{[1
]}

Wang, Yi-Ming ^{[1
]}

Drljevic, Amela ^{[1
]}

Rauniyar, Vivek ^{[1
]}

Phipps, Robert J. ^{[1
]}

Toste, F. Dean ^{[1
]}

机构：

[1] Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA

来源：

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA | 2013年 / 110卷 / 34期

关键词：

asymmetric; organocatalysis; hydrogen-bonding; BETA-FLUOROAMINES; ASYMMETRIC FLUORINATION; EPOXIDATION; STRATEGY; ACCESS;

D O I：

10.1073/pnas.1304346110

中图分类号：

O [数理科学和化学]; P [天文学、地球科学]; Q [生物科学]; N [自然科学总论];

学科分类号：

07 ; 0710 ; 09 ;

摘要：

We report a catalytic enantioselective electrophilic fluorination of alkenes to form tertiary and quaternary C(sp3)-F bonds and generate beta-amino- and beta-aryl-allylic fluorides. The reaction takes advantage of the ability of chiral phosphate anions to serve as solid-liquid phase transfer catalysts and hydrogen bond with directing groups on the substrate. A variety of heterocyclic, carbocyclic, and acyclic alkenes react with good to excellent yields and high enantioselectivities. Further, we demonstrate a one-pot, tandem dihalogenation-cyclization reaction, using the same catalytic system twice in series, with an analogous electrophilic brominating reagent in the second step.

引用

页码：13729 / 13733

页数：5

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