Highly Regio- and Stereoselective Synthesis of Tetracyclic Indolenoisoxazolidines via Intramolecular 1,3-Dipolar Nitrone Cycloadditions

被引：5

作者：

Bakthadoss, Manickam ^{[1
,2
]}

Sivakumar, Govindan ^{[1
]}

Sharada, Duddu S. ^{[3
]}

机构：

[1] Univ Madras, Dept Organ Chem, Madras 600025, Tamil Nadu, India

[2] Pondicherry Univ, Dept Chem, Pondicherry 605014, India

[3] Indian Inst Technol, Dept Chem, Hyderabad 502205, Andhra Pradesh, India

来源：

SYNTHESIS-STUTTGART | 2013年 / 45卷 / 02期

关键词：

fused-ring systems; indoles; 1,3-dipolar cycloaddition; stereoselectivity; regioselectivity; BAYLIS-HILLMAN REACTION; ONE-POT CONVERSION; ALKALOIDS; ADDUCTS; FACILE;

D O I：

10.1055/s-0032-1317928

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A facile method for the simple synthesis of tetracyclic indoloisoxazolidine frameworks from Baylis-Hillman derivatives through formation of nitrones in situ followed by an intramolecular [3+2]-dipolar cycloaddition reaction sequence is described. High regio- and stereoselectivity, excellent yields, together with the creation of two rings and three contiguous stereogenic centers including one all carbon quaternary center, are the salient features of the present method.

引用

页码：237 / 245

页数：9

共 38 条

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