Chiral phosphoric acid catalyzed enantioselective annulation of acyclic enecarbamates to in situ-generated ortho-quinone methides

被引：29

作者：

Gharui, Chandan ^{[1
]}

Singh, Shreya ^{[1
]}

Pan, Subhas Chandra ^{[1
]}

机构：

[1] Indian Inst Technol Guwahati, Dept Chem, Gauhati 781039, India

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2017年 / 15卷 / 35期

关键词：

MICHAEL-MICHAEL CASCADE; HIGHLY SUBSTITUTED CHROMANS; SENSITIVE POTASSIUM CHANNEL; ASYMMETRIC-SYNTHESIS; DIASTEREOSELECTIVE SYNTHESIS; ADDITION-REACTIONS; CYCLOADDITION; STRATEGY; ALKYLATION; ALCOHOLS;

D O I：

10.1039/c7ob01766a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first organocatalytic asymmetric reaction of acyclic enecarba-mates with o-quinone methides is disclosed. BINOL-based phosphoric acid catalysts were found to be suitable for the annulation reaction. With 10 mol% of the TRIP catalyst, high yields as well as excellent diastereo- and enantioselectivities are achieved for a variety of 2,3,4-trisubstituted chroman products.

引用

页码：7272 / 7276

页数：5

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