Influence of A1,3 Strain on the Stereochemical Outcome of Acid-Mediated Amido Cyclization in the Synthesis of 2-(4-Methoxyphenyl)-3,4-(dihydroxy)piperidines

被引：3

作者：

Ramakrishna, Katakam ^{[1
]}

Jagadeesh, Yerri ^{[1
]}

Ramakrishna, K. V. S. ^{[2
]}

Rao, Joshi Laxmikanth ^{[3
]}

Rao, Batchu Venkateswara ^{[1
]}

机构：

[1] Indian Inst Chem Technol, CSIR, Organ & Biomol Chem Div, Hyderabad 500607, Andhra Pradesh, India

[2] Indian Inst Chem Technol, CSIR, NMR Div, Hyderabad 500607, Andhra Pradesh, India

[3] Indian Inst Chem Technol, CSR, I & PC Div, Hyderabad 500607, Andhra Pradesh, India

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 2016卷 / 09期

关键词：

Asymmetric synthesis; Azasugars; Hydroxylation; Cyclization; Diastereoselectivity; GLYCOSIDASE INHIBITORS; RADICAMINE-B; PIPERIDINE; ALKALOIDS; EFFICIENT;

D O I：

10.1002/ejoc.201501577

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of 2-(4-methoxyphenyl)-3,4-(dihydroxy) piperidines was accomplished by using ethyl p-methoxycinnamate as the starting material and an acid-mediated amido cyclization reaction as the key step. This short and straightforward strategy avoids extra steps to create the chiral center and does not require a leaving group at the benzylic carbon. This study also showed that the stereochemical outcome of the cyclization reaction is influenced more by allylic 1,3-strain (A(1,3) strain) than by the participation of a neighboring group.

引用

页码：1693 / 1701

页数：9

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