Pinacol rearrangement for constructing asymmetric centers adjacent to heterocycles

Shinohara, Tomoichi; Suzuki, Keisuke

doi:10.1016/s0040-4039(02)01626-x

Cited by 31 publications

(7 citation statements)

References 18 publications

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“…Carboxylic acid derivatives with indol systems are important chemical architectures in medicinal chemistry and agrochemicals 46. Unfortunately, direct access to these molecular motifs by conventional catalytic Michael additions is frequently not possible because of the intrinsic reluctance of common unsaturated carboxylic derivatives to undergo 1,4‐additions with indoles 47…”

Section: Reactions With Cc Multiple Bondsmentioning

confidence: 99%

Catalytic Functionalization of Indoles in a New Dimension

2009

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140 years ago Adolf von Baeyer proposed the structure of a heteroaromatic compound which revolutionized organic and medical chemistry: indole. After more than a century, indole itself and the complexity of naturally occurring indole derivatives continue to inspire and influence developments in synthetic chemistry. In particular, the ubiquitous presence of indole rings in pharmaceuticals, agrochemicals, and functional materials are testament to the ever increasing interest in the design of mild and efficient synthetic routes to functionalized indole derivatives. This Review emphasizes the achievements in the selective catalytic functionalization of indoles (C-C bond-forming processes) over the last four years.

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Section: Reactions With Cc Multiple Bondsmentioning

confidence: 99%

Catalytic Functionalization of Indoles in a New Dimension

2009

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“…Both Lewis acids and bases can promote the 1,2-migration with loss of leaving group such as OMs or OTs (Scheme 9). 11 Compared with the simple sulfur-based rearrangement, this type of reaction is more regioselective and possesses broader substrate scope in ring expansions. For example, the adducts derived from the anion of methoxymethyl phenyl sulfone and cyclic ketones rearrange on addition of Lewis acid (Scheme 10).…”

Section: Sulfonates As Leaving Groupmentioning

confidence: 99%

3.16 The Semipinacol Rearrangements

Wang¹,

Tu²,

Tang³

2014

Comprehensive Organic Synthesis II

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“…To obtain relationship between physicochemical parameters and anticancer activity for the present series, we have carried out QSAR study by Hansch's LFER method (Tiwari et al, 2006;Hansch and Leo, 1995). LogGI 50 ?…”

Section: Qsar Studymentioning

confidence: 99%

Synthesis, characterization, anticancer activity, and QSAR-studies of some new tetrahydropyrimidines

et al. 2010

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Several new substituted 1,2,3,4 tetrahydropyrimidine derivatives have been synthesized and evaluated for their in vitro anticancer activity on various cell lines. Some of the molecules have exhibited significantly potent inhibition on several cell lines. To find out inter correlation between anticancer activity and molecular descriptors, QSAR study was carried out. Molecular descriptors used for the study were ClogP (lipophilic), CMR (steric), and polarity (electronic). Anticancer activity is expressed in the form of LogGI 50? . Activity on different cell lines was independently correlated with molecular descriptors. On the basis of the results, significant correlation between anticancer activity on some of the cell lines and molecular descriptor was observed.

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Pinacol rearrangement for constructing asymmetric centers adjacent to heterocycles

Cited by 31 publications

References 18 publications

Catalytic Functionalization of Indoles in a New Dimension

Catalytic Functionalization of Indoles in a New Dimension

3.16 The Semipinacol Rearrangements

Synthesis, characterization, anticancer activity, and QSAR-studies of some new tetrahydropyrimidines

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