Design and Synthesis of Benzosultine-sulfone as a o-Xylylene Precursor via Cross-enyne Metathesis and Rongalite: Further Expansion to Polycyclics via Regioselective Diels-Alder Reaction

被引：77

作者：

Kotha, Sambasivarao ^{[1
]}

Chavan, Arjun S. ^{[1
]}

机构：

[1] Indian Inst Technol, Dept Chem, Bombay 400076, Maharashtra, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 75卷 / 12期

关键词：

ALPHA-AMINO-ACID; CYCLOBUTANE AROMATIC COMPOUNDS; INTRAMOLECULAR CYCLOADDITION REACTIONS; SODIUM FORMALDEHYDE SULFOXYLATE; DIVERSITY-ORIENTED APPROACH; ORTHO-QUINODIMETHANES; ORGANIC-SYNTHESIS; COUPLING REACTION; NATURAL-PRODUCTS; TIC DERIVATIVES;

D O I：

10.1021/jo100655c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Benzosultine-sulfone 5 has been prepared as a o-xylylene or o-quinodimethane precursor by utilization of rongalite. Thermal activation of this hybrid molecule 5 has resulted a new sulfone-based building block 6. Building block 5 is a suitable precursor for the synthesis of unsymmetrically functionalized polycyclics through Diels-Alder (DA) chemistry. The dibromosulfone 24 and benzosultine-sulfone 5 has also been used for the synthesis of various sulfone based unnatural a-amino acid (AAA) derivatives.

引用

页码：4319 / 4322

页数：4

共 3 条

[1] Design and Synthesis of Angularly Annulated Spirocyclics via Enyne Metathesis and the Diels-Alder Reaction as Key Steps
Kotha, Sambasivarao
Ali, Rashid
Tiwari, Arti
SYNTHESIS-STUTTGART, 2014, 46 (18): : 2471 - 2480
[2] Diversity-Oriented Synthesis of Biaryl Derivatives Using Cross-Enyne Metathesis, Diels-Alder Reaction, and Suzuki-Miyaura Cross-Coupling as Key Steps
Kotha, Sambasivarao
Seema, Vittal
SYNLETT, 2011, (16) : 2329 - 2334
[3] Design and synthesis of polycyclic sulfones via Diels-Alder reaction and ring-rearrangement metathesis as key steps
Kotha, Sambasivarao
Gunta, Rama
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2015, 11 : 1373 - 1378

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