Stereochemical Prins cyclization: electronic versus steric effects on the synthesis of 2,4,6-trisubstituted tetrahydropyran rings

Chan, Kok-Ping; Seow, Ai-Hua; Loh, Teck‐Peng

doi:10.1016/j.tetlet.2006.11.023

Cited by 36 publications

(10 citation statements)

References 28 publications

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“…202 Especially noteworthy was the excellent stereoselectivity observed where only the all-cis configuration products were obtained, except in specific cases. 203 In order to apply the methodology to an enantioselective synthesis, optically active alcohols were engaged in the process; indium(III) bromide as a weaker Lewis acid turned out to be more efficient than indium(III) triflate to reduce the rate of epimerization of the homoallylic alcohol 120, which led to an 84% enantiomeric excess of a precursor (121) of (-)-centrolobine (Scheme 58). With stoichiometric indium(III) chloride, but in the absence of chlorotrimethylsilane, the enantiomeric excess was increased to 90%.…”

Section: Prins-type and Related Reactionsmentioning

confidence: 99%

Recent Advances in Indium-Promoted Organic Reactions

Augé¹,

Lubin‐Germain²,

Uziel³

2007

Synthesis

162

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I n d i u m -P r o m o t e d O r g a n i c R e a c t i o n sAbstract: This review deals with organic reactions which are promoted by indium metal or indium salts, with a focus on recent advances in stoichiometric and catalytic pathways. Applications to transmetalations, cross-coupling reactions and carboindation, in which an organoindium species may be postulated, are highlighted, as well as the reactions in which a radical is the key intermediate. Special attention is placed on the role of indium metal as a reducer, and on the Lewis acidity of indium salts in catalytic processes.

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Section: Prins-type and Related Reactionsmentioning

confidence: 99%

Recent Advances in Indium-Promoted Organic Reactions

Augé¹,

Lubin‐Germain²,

Uziel³

2007

Synthesis

162

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“…Generally, tetrahydropyran derivatives are synthesized by Prins cyclization using an acid catalyst [20][21][22][23]. Alternatively they can be formed by hetero-Diels-Alder cyclization [24][25][26].…”

Section: Introductionmentioning

confidence: 99%

Three-component synthesis of novel trifluoromethyl-containing tetrahydropyran derivatives

Zhang

Cao

et al. 2009

Journal of Fluorine Chemistry

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“…By controlling the reaction conditions, the intramolecular allylation of internal aldehyde with allylstannanes, 19 allylsilanes, 20 with all stereogenic centers installed as expected. funiculosin, 2 (+)-ambruticin, 3 (+)-4,5-deoxyneodolabelline, 4 and methyl sarcophytoate ( Figure 5.1…”

Section: Resultsmentioning

confidence: 67%

“…The results are summarized inTable 2.1 and Table 2.2. and 12 were selected to perform a series of chemical transformations to explore the synthetic versatilities of our dibromo-THP rings (Scheme 2.19). As expected, 18 was readily obtained with a selective double bond via From Electronic Effect As mentioned above, our group's trans Prins cyclization utilized the electronic directing effect leading to a moderate trans selectivity 20. Here, we progress further in From the point of view of steric effect, our A value strategy failed to provide us with a novel trans Prins cyclization reaction.…”

mentioning

confidence: 62%

Development of new synthetic methods towards prins cyclization

Liu¹

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Backbones 1 1.2 General Discussion on Prins Cyclization 4 1.3 Development of Novel Prins Cyclization Reactions 16 Chapter 2 : DEVELOPMENT OF NOVEL TRANS PRINS CYCLIZATION REACTION 2.1 Introduction 17 2.2 General Methods for Construction of 2,6-trans tetrahydropyrans 18 2.3 Prins Cyclization to 2,6-trans tetrahydropyran 23 2.4 Development of Novel trans Prins Cyclization 28 2.5 Conclusion 37 Chapter 3 : FRIEDEL-CRAFTS-PRINS CASCADE CONDENSATION OF PROPARGYLIC EPOXIDES WITH ALEHYDES 3.1 Introduction 38 ATTENTION: The Singapore Copyright Act applies to the use of this document. Nanyang Technological University Library iii 3.2 Cascade Reaction to Make Polycyclic Frameworks 3.3 Results and Discussion 47 3.4 Conclusion Chapter 4 : FRIEDEL-CRAFTS-PRINS CASCADE CONDENSATION OF ALLYLIC EPOXIDES WITH ALEHYDES 4.1 Introduction 4.2 Results and Discussion 4.3 Conclusion

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Stereochemical Prins cyclization: electronic versus steric effects on the synthesis of 2,4,6-trisubstituted tetrahydropyran rings

Cited by 36 publications

References 28 publications

Recent Advances in Indium-Promoted Organic Reactions

Recent Advances in Indium-Promoted Organic Reactions

Three-component synthesis of novel trifluoromethyl-containing tetrahydropyran derivatives

Development of new synthetic methods towards prins cyclization

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