Intramolecular [3+2] nitrone cycloaddition reaction: highly regio and diastereoselective synthesis of bicyclo[3.2.1]octane scaffolds

被引：4

作者：

Bakthadoss, Manickam ^{[1
]}

Mushaf, Mohammad ^{[1
]}

机构：

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

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2020年 / 18卷 / 47期

关键词：

X=Y-ZH SYSTEMS; POTENTIAL 1,3-DIPOLES; N; N-DISUBSTITUTED HYDROXYLAMINES; STEREOSELECTIVE-SYNTHESIS; HYDROGEN-PEROXIDE; CLASS-2; PROCESSES; STERIC FACTORS; DERIVATIVES; CONSTRUCTION; GENERATION;

D O I：

10.1039/d0ob01960g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A regio and diastereoselective strategy has been developed for the synthesis of complex bicyclo[3.2.1]octane scaffolds from the reaction of readily accessible vinylogous carbonates with N-substituted hydroxylamine hydrochlorides via intramolecular 1,3-dipolar nitrone cycloaddition reaction. Wide varieties of bicyclic isoxazolidines were synthesized in high yields under catalyst free conditions through a highly efficient and operationally simple protocol.

引用

页码：9653 / 9659

页数：7

共 50 条

[1] A formal [3+2] cycloaddition for the synthesis of bicyclo[3.2.1]octanes
Orac, Crina M.
Bergmeier, Stephen C.
TETRAHEDRON LETTERS, 2009, 50 (12) : 1261 - 1263
[2] Diastereoselective construction of highly functionalized tetrahydroquinolinoisoxazole scaffolds via intramolecular nitrone cycloaddition
Bakthadoss, Manickam
Devaraj, Anthonisamy
TETRAHEDRON LETTERS, 2015, 56 (25) : 3954 - 3960
[3] Studies of intramolecular nitrone-alkene cycloaddition reaction: Regio- and diastereoselective synthesis of chlorinated isoxazolidines
Roy, Brindaban
De, Rajendra Narayan
INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 2013, 52 (01): : 146 - 152
[4] Phosphine-catalyzed intramolecular formal [3+2] cycloaddition for highly diastereoselective synthesis of bicyclo[n.3.0] compounds
Ye, Long-Wu
Sun, Xiu-Li
Wang, Qing-Gang
Tang, Yong
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (31) : 5951 - 5954
[5] INTRAMOLECULAR [3+2] NITRONE-ALKYNE CYCLOADDITION
KANG, HY
CHO, YS
KOH, HY
CHANG, MH
TETRAHEDRON LETTERS, 1991, 32 (24) : 2779 - 2782
[6] A Regio- and Diastereoselective Intramolecular Nitrone Cycloaddition for Practical 3-and 2,3-Disubstituted Piperidine Synthesis from γ-Butyrolactone
Stephens, Benjamin E.
Liu, Fei
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (01): : 254 - 263
[7] BICYCLO[3.2.1]OCT-6-ENES VIA (3+2)CYCLOADDITION
GRAY, BD
MCMILLAN, CM
MILLER, JA
MOORE, M
TETRAHEDRON LETTERS, 1987, 28 (02) : 235 - 238
[8] Highly Regio- and Diastereoselective Anionic [3+2] Cycloaddition under Phase Transfer Catalytic Conditions
Gembus, Vincent
Postikova, Svetlana
Levacher, Vincent
Briere, Jean-Francois
JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (10): : 4194 - 4199
[9] LIQUID-CRYSTAL CONTROL, HIGHLY DIASTEREOSELECTIVE [3+2] NITRONE-OLEFIN CYCLOADDITION IN SMECTIC SOLVENT
KANSUI, H
KUNIEDA, T
TETRAHEDRON LETTERS, 1995, 36 (33) : 5899 - 5902
[10] Tandem Michael addition/intramolecular isocyanide [3+2] cycloaddition: highly diastereoselective one pot synthesis of fused oxazolines
Zhang, Lingjuan
Xu, Xianxiu
Tan, Jing
Pan, Ling
Xia, Wenming
Liu, Qun
CHEMICAL COMMUNICATIONS, 2010, 46 (19) : 3357 - 3359

← 1 2 3 4 5 →