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Literature DB >> 26594355

Synthesis of 1,5-Dioxocanes via the Two-Fold C-O Bond Forming Nucleophilic 4+4-Cyclodimerization of Cycloprop-2-en-1-ylmethanols.

Andrew Edwards¹, Trevor Bennin², Marina Rubina¹, Michael Rubin³.

Abstract

An efficient [4+4] cyclodimerization of cyclopropenemethanols operating via a two-fold strain release-driven addition of alkoxides across the double bond of cyclopropenes was investigated. This chemo- and diastereoselective transformation provided previously unknown 2,7-dioxatricyclo[7.1.0.04,6]decane scaffolds.

Entities: Chemical Gene

Year: 2015 PMID： 26594355 PMCID： PMC4652585 DOI： 10.1039/C5RA14077C

Source DB: PubMed Journal: RSC Adv ISSN： 2046-2069 Impact factor: 3.361

16 in total

1. Catalytic enantioselective hydrostannation of cyclopropenes.

Authors: Marina Rubina; Michael Rubin; Vladimir Gevorgyan
Journal: J Am Chem Soc Date: 2004-03-31 Impact factor: 15.419

2. Formal nucleophilic substitution of bromocyclopropanes with amides en route to conformationally constrained β-amino acid derivatives.

Authors: Anthony R Prosser; Joseph E Banning; Marina Rubina; Michael Rubin
Journal: Org Lett Date: 2010-09-17 Impact factor: 6.005

3. Challenge to detect 1,4-zwitterions spectroscopically in a ketene-alkene reaction.

Authors: Takahisa Machiguchi; Junko Okamoto; Yumiko Morita; Toshio Hasegawa; Shinichi Yamabe; Tsutomu Minato
Journal: J Am Chem Soc Date: 2006-01-11 Impact factor: 15.419

4. Intermolecular tandem Pd-catalyzed cross-coupling/[4+4] and [4+2] cycloadditions: a one-pot, five-component assembly of bicyclo[6.4.0]dodecanes.

Authors: Phil Ho Lee; Kooyeon Lee
Journal: Angew Chem Int Ed Engl Date: 2005-05-20 Impact factor: 15.336

5. In situ generation of vinyl allenes and its applications to one-pot assembly of cyclohexene, cyclooctadiene, 3,7-nonadienone, and bicyclo[6.4.0]dodecene derivatives with palladium-catalyzed multicomponent reactions.

Authors: Phil Ho Lee; Kooyeon Lee; Youngjin Kang
Journal: J Am Chem Soc Date: 2006-02-01 Impact factor: 15.419

6. Thermodynamic control of diastereoselectivity in the formal nucleophilic substitution of bromocyclopropanes.

Authors: Joseph E Banning; Anthony R Prosser; Michael Rubin
Journal: Org Lett Date: 2010-04-02 Impact factor: 6.005

7. Diastereoselectivity control in formal nucleophilic substitution of bromocyclopropanes with oxygen- and sulfur-based nucleophiles.

Authors: Joseph E Banning; Anthony R Prosser; Bassam K Alnasleh; Jason Smarker; Marina Rubina; Michael Rubin
Journal: J Org Chem Date: 2011-04-14 Impact factor: 4.354

8. Regioselective photodimerization of pyridyl-butadienes within cucurbit[8]uril cavities.

Authors: Murthy V S N Maddipatla; Mahesh Pattabiraman; Arunkumar Natarajan; Karan Srivastav; Joel T Mague; V Ramamurthy
Journal: Org Biomol Chem Date: 2012-10-29 Impact factor: 3.876

9. Dual control of the selectivity in the formal nucleophilic substitution of bromocyclopropanes en route to densely functionalized, chirally rich cyclopropyl derivatives.

Authors: Pavel Ryabchuk; Andrew Edwards; Nikolay Gerasimchuk; Marina Rubina; Michael Rubin
Journal: Org Lett Date: 2013-11-21 Impact factor: 6.005