Asymmetric Roadmap to Diverse Polycyclic Benzopyrans via Phosphine-Catalyzed Enantioselective [4+2]-Annulation Reaction

被引：43

作者：

Danda, Adithi ^{[1
,2
]}

Kesava-Reddy, Naredla ^{[1
]}

Golz, Christopher ^{[2
]}

Strohmann, Carsten ^{[2
]}

Kumar, Kamal ^{[1
]}

机构：

[1] Max Planck Inst Mol Physiol, Abt Chem Biol, Otto Hahn Str 11, D-44227 Dortmund, Germany

[2] Tech Univ Dortmund, Fak Chem & Chem Biol, Otto Hahn Str 6, D-44221 Dortmund, Germany

来源：

ORGANIC LETTERS | 2016年 / 18卷 / 11期

关键词：

DIELS-ALDER REACTION; 1,3-BIS-SILYL ENOL ETHERS; N-ACYL AMINOPHOSPHINES; 4+2 ANNULATION; NATURAL-PRODUCTS; DOMINO REACTIONS; DRUG DISCOVERY; ALLENOATES; CHROMONE; CYCLOADDITIONS;

D O I：

10.1021/acs.orglett.6b01030

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The catalytic addition of the amino acid derived bifunctional N-acylaminophosphine to an alpha-substituted allene ester generated a zwitterionic dipole that engaged the vinylogous ester function of 3-cyano-chromones in a [4 + 2] annulation reaction to deliver tetrahydroxanthones embodying three consecutive chiral centers in high yields and with excellent enantioselectivities. The established asymmetric synthesis Anther paves the way to two different classes of complex, sp(3)-rich tetracyclic benzopyrans via efficient cascade reactions.

引用

页码：2632 / 2635

页数：4

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