Application of organolithium and related reagents in synthesis. Part 25: Novel specific synthesis of the 4-arylisochroman-3-acetic acids via conversion of benzoic acids

被引：8

作者：

Bieniek, A ^{[1
]}

Epsztajn, J ^{[1
]}

Kowalska, JA ^{[1
]}

Malinowski, Z ^{[1
]}

机构：

[1] Univ Lodz, Inst Chem, Dept Organ Chem, PL-90136 Lodz, Poland

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 52期

关键词：

benzanilides; metallations; isochromans;

D O I：

10.1016/S0040-4039(01)02043-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The transformation of the benzanilides 1 into 4-arylisochroman-3-acetic acids 8 applying the following sequence of reactions is described. At first, the 3-arylphthalides 3 were obtained via metallation [n-BuLi] of benzanilides I and subsequent treatment of the generated bis-lithiated anilides 2 with aromatic aldehydes. Next, the 3-arylphthalides 3 were reduced [LiBH4] to phthalanes 5 and then, via reductive metallation [Li/C10H8] and reaction of the generated is-lithiated species 6 with dimethylformamide. 3-hydroxy-4-arylisochromans 7 were produced. In the final step the isochromans 7 were treated with 1-methoxy-1-trimethylsilyloxyethene in the presence of titanium tetrachloride and furnished 4-arylisochromans-3-acetic acid methyl esters 8 as trans stereoisomers (Psi -e/e). (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：9293 / 9295

页数：3

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