Stereocontrolled synthesis of acyclic terpenoids via N-ylide [2,3]rearrangement of ammonium salts with the stereodefined isoprene unit

Honda, Kiyoshi; Tabuchi, Masayuki; Kurokawa, Hiroki; Asami, Masatoshi; Inoue, Seiichi

doi:10.1039/b201304e

Cited by 9 publications

(2 citation statements)

References 19 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Terpenoids such as sinensal and retinol have been prepared by stereoselective [2,3]-rearrangement of ammonium ylids. 37 Coldham et al reported that tandem salt-formation-[2,3]-rearrangements are observed when N-allyl(alkyl) glycine esters are treated with an alkylating agent in polar solvent, thus obviating the need for isolation of the intermediate ammonium salt (Scheme 38). 38 As mentioned above, the diastereoselectivity of the rearrangements is modest.…”

Section: [23]-rearrangementsmentioning

confidence: 99%

Sigmatropic rearrangements of ‘onium’ ylids

Sweeney

2009

Chem. Soc. Rev.

210

View full text Add to dashboard Cite

Rearrangement reactions occupy a special place within the canon of organic synthesis, by virtue of the inherently high efficiency of chemical processes which form and break bonds by redistribution of electrons around a retained atomic framework. Within the broader class, sigmatropic rearrangements are chemical processes defined by mechanisms involving unimolecular migration of sigma-bonds with concomitant redistribution of one or more pi-bonds. Sigmatropic processes may involve uncharged or charged species, with the charges located on carbon or heteroatoms; the latter reaction type is the subject of this tutorial review.

show abstract

Section: [23]-rearrangementsmentioning

confidence: 99%

Sigmatropic rearrangements of ‘onium’ ylids

Sweeney

2009

Chem. Soc. Rev.

210

View full text Add to dashboard Cite

show abstract

“…About Vitamin A, AIPHOS recognized 18 strategic sites including five RSS, 21 [38], 24 [39], 28 [40], 36 [41,42], and 38 [43] (Fig. 11).…”

Section: 0777mentioning

confidence: 99%

Development of Evaluation Model for Strategic Sites in Synthetic Route Design System AIPHOS

Tanaka¹,

Kawai²,

Matsumoto³

et al. 2008

J. Comput. Aided Chem.

View full text Add to dashboard Cite

An evaluation technique was developed to prioritize synthetic strategic sites (a set of bonds to make precursors by cut and connection) for the purpose of effective retro-synthesis in synthetic route design system, AIPHOS. In this paper, the relationship between the strategic sites proposed by AIPHOS and the reaction centers in reaction databases was discussed. The correlation has been analyzed by logistic regression analysis (LoRA) with molecular centrality, bond dissociation energy (BDE), and the number of bonds. We used the equation to clarify the importance of synthetic strategy sites. The correlation models showed high similarity among three reaction databases. In addition, from the model, reaction centers in reaction databases were found to be located in the center of the whole structures, to have fewer bonds, and to have smaller bond dissociation energies.

show abstract

[2,3]‐Rearrangements of Ammonium Zwitterions

Bao

Tambar

2015

Molecular Rearrangements in Organic Synthesis

View full text Add to dashboard Cite

Stereocontrolled synthesis of acyclic terpenoids via N-ylide [2,3]rearrangement of ammonium salts with the stereodefined isoprene unit

Cited by 9 publications

References 19 publications

Sigmatropic rearrangements of ‘onium’ ylids

Sigmatropic rearrangements of ‘onium’ ylids

Development of Evaluation Model for Strategic Sites in Synthetic Route Design System AIPHOS

[2,3]‐Rearrangements of Ammonium Zwitterions

Contact Info

Product

Resources

About