Catalyst-Free Intramolecular Formal Carbon Insertion into σ-C-C Bonds: A New Approach toward Phenanthrols and Naphthols

被引：65

作者：

Xia, Ying ^{[1
,2
]}

Qu, Peiyuan ^{[1
,2
]}

Liu, Zhenxing ^{[1
,2
]}

Ge, Rui ^{[1
,2
]}

Xiao, Qing ^{[1
,2
]}

Zhang, Yan ^{[1
,2
]}

Wang, Jianbo ^{[1
,2
]}

机构：

[1] Peking Univ, BNLMS, Minist Educ, Coll Chem, Beijing 100871, Peoples R China

[2] Peking Univ, Key Lab Bioorgan Chem & Mol Engn, Minist Educ, Coll Chem, Beijing 100871, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2013年 / 52卷 / 09期

关键词：

1,2-shift; cyclization; diazo compounds; insertion; hydrocarbons; ASYMMETRIC ROSKAMP REACTION; BETA-KETO-ESTERS; AROMATIC-ALDEHYDES; RING-EXPANSION; ENANTIOSELECTIVE SYNTHESIS; DIRECTED ORTHO; POLYSUBSTITUTED NAPHTHOLS; REGIOSPECIFIC SYNTHESIS; TOSYLHYDRAZONE SALTS; QUATERNARY CENTER;

D O I：

10.1002/anie.201209269

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The different reactivity of two kinds of carbonyl groups in keto aldehyde substrates has been exploited for the synthesis of phenanthrols, naphthols, and their heteroatom-containing analogues. Key to this highly efficient and robust methodology is the catalyst-free intramolecular formal diazo carbon insertion of N-tosylhydrazones into keto C-C bonds (see scheme). Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：2543 / 2546

页数：4

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