Enantioselective Reactions of 2-Sulfonylalkyl Phenols with Allenic Esters: Dynamic Kinetic Resolution and [4+2] Cycloaddition Involving ortho-Quinone Methide Intermediates

被引：106

作者：

Chen, Ping ^{[1
,2
]}

Wang, Kai ^{[1
,2
]}

Guo, Wengang ^{[1
]}

Liu, Xianghui ^{[1
,2
]}

Liu, Yan ^{[1
]}

Li, Can ^{[1
]}

机构：

[1] Chinese Acad Sci, State Key Lab Catalysis, Dalian Inst Chem Phys, 457 Zhongshan Rd, Dalian 116023, Peoples R China

[2] Grad Univ, Chinese Acad Sci, Beijing 100049, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2017年 / 56卷 / 13期

关键词：

benzylic sulfones; chromans; cycloaddition; dynamic kinetic resolution; ortho-quinone methides; CATALYTIC ASYMMETRIC-SYNTHESIS; O-HYDROXYBENZYL ALCOHOLS; BAYLIS-HILLMAN REACTION; IN-SITU; CONJUGATE ADDITION; ALLYLIC SULFONES; ACID CATALYSIS; ALLENOATES; IMINES; ANNULATIONS;

D O I：

10.1002/anie.201700250

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We report herein a dynamic kinetic resolution (DKR) involving ortho-quinone methide (o-QM) intermediates. In the presence of Et3N and the cinchonine-derived nucleophilic catalyst D, the DKR of 2-sulfonylalkyl phenols with allenic esters afforded chiral benzylic sulfones in 57-79% yield with good to excellent enantioselectivity (85-95% ee). Furthermore, with 2-(tosylmethyl) sesamols or 2-(tosylmethyl)-naphthols, from which stable o-QM substrates can be generated, a formal [4+2] cycloaddition delivered 4-aryl- or alkyl-substituted chromans with excellent enantioselectivity (88-97% ee).

引用

页码：3689 / 3693

页数：5

共 34 条

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[6] Enantioselective Formal [4+2] Annulation of ortho-Quinone Methides with ortho-Hydroxyphenyl α,β-Unsaturated Compounds
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[7] Lewis Acid Catalyzed [4+2] Cycloaddition of N-Tosylhydrazones with ortho-Quinone Methides
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[8] Dearomative [4+2] Cycloaddition of Oxindole-Embedded ortho-Quinone Methides with 2,5-Dialkylfurans
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