Asymmetric Dearomatization of Phthalazines by Anion-Binding Catalysis

被引：4

作者：

Velazquez, Marta ^{[1
,2
]}

Fernandez, Rosario ^{[1
,2
]}

Lassaletta, Jose M. ^{[3
,4
]}

Monge, David ^{[1
,2
]}

机构：

[1] Univ Seville, Fac Quim, Dept Quim Organ, Seville 41012, Spain

[2] Ctr Innovac Quim Avanzada ORFEO CINQA, Seville 41012, Spain

[3] CSIC US, Inst Invest Quim, Seville 41092, Spain

[4] Ctr Innovac Quim Avanzada ORFEO CINQA, Seville 41092, Spain

来源：

ORGANIC LETTERS | 2023年 / 25卷 / 49期

关键词：

NUCLEOPHILIC DEAROMATIZATION; CYCLOADDITION; INHIBITORS;

D O I：

10.1021/acs.orglett.3c03325

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A straightforward methodology for the enantioselective synthesis of 1,2-dihydrophthalazines via dearomatization of phthalazines by anion-binding catalysis has been developed. The process involves the Mannich-type addition of silyl ketene acetals to in situ generated N-acylphthalazinium chlorides using a tert-leucine derived thiourea as a H-bond donor catalyst. Ensuing selective and high-yielding transformations provide appealing dihydro- and tetrahydro-phthalazines, phthalazones, and piperazic acid homologues, en route to biologically relevant molecules.

引用

页码：8797 / 8802

页数：6

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