Evolving Organic Synthesis Fostered by the Pluripotent Phenylsulfone Moiety

被引：353

作者：

El-Awa, Ahmad ^{[1
]}

Noshi, Mohammad N. ^{[1
]}

du Jourdin, Xavier Mollat ^{[1
]}

Fuchs, Philip L. ^{[1
]}

机构：

[1] Purdue Univ, Dept Chem, W Lafayette, IN 47907 USA

来源：

CHEMICAL REVIEWS | 2009年 / 109卷 / 06期

关键词：

CONVERGENT TOTAL-SYNTHESIS; N-ACYLIMINIUM IONS; 2-BENZENESULFONYL CYCLIC ETHERS; HIGHLY EFFICIENT SYNTHESIS; FORMAL TOTAL-SYNTHESIS; TRANS-FUSED TETRAHYDROPYRANS; CONJUGATE-ADDITION REACTIONS; ACYLVINYL ANION EQUIVALENTS; DOUBLE ELIMINATION-REACTION; CATION-MEDIATED SYNTHESIS;

D O I：

10.1021/cr800309r

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Some significant factors associated with evolving organic synthesis promoted by the pluripotent phenylsulfone moiety are discussed. The attribute of the phenylsulfone functional group included economical and stable functionality for purification, while UV chromophore of the aryl sulfone allowed easy reaction monitoring by thin-layer chromatography (TLC) and high performance liquid chromatography (HPLC). The strong inductive ability of the sulfone group enhanced the dipolar character of vinyl sulfones and inductively weakens the S-C σ-bond of sp 3-hybridized substrates. Lone-pair assistance of proximal heteroatom, which facilitated departure of sulfinate by scission of the C-S bond, was termed as 'chemical chameleon'. It was concluded that pluripotent phenyl sulfone can be used by synthetic organic chemist as a versatile functional group.

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页码：2315 / 2349

页数：35

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