Literature DB >> 22125343

Stereochemical investigation of conjugate additions of carbon- and heteronucleophiles to ring-substituted nitrosocyclohexenes.

Ritobroto Sengupta1, Jason A Witek, Steven M Weinreb.   

Abstract

Intermolecular Michael-type conjugate additions of some in situ-generated ring-substituted nitrosocyclohexenes with both carbon- and heteronucleophiles have been found to be highly stereoselective, leading predominantly (or exclusively) to products resulting from axial attack on a half-chair conformation of the nitrosoalkene substrate.

Entities:  

Year:  2011        PMID: 22125343      PMCID: PMC3224044          DOI: 10.1016/j.tet.2011.08.054

Source DB:  PubMed          Journal:  Tetrahedron        ISSN: 0040-4020            Impact factor:   2.457


  8 in total

1.  Construction of bridged and fused ring systems via intramolecular Michael reactions of vinylnitroso compounds.

Authors:  Ilia Korboukh; Praveen Kumar; Steven M Weinreb
Journal:  J Am Chem Soc       Date:  2007-08-03       Impact factor: 15.419

2.  Nucleophilic α-arylation and α-alkylation of ketones by polarity inversion of N-alkoxyenamines: entry to the umpolung reaction at the α-carbon position of carbonyl compounds.

Authors:  Tetsuya Miyoshi; Takayuki Miyakawa; Masafumi Ueda; Okiko Miyata
Journal:  Angew Chem Int Ed Engl       Date:  2010-11-23       Impact factor: 15.336

3.  Efficient methodology for alkylation of vinylnitroso compounds with carbon nucleophiles.

Authors:  Puhui Li; Max M Majireck; Jason A Witek; Steven M Weinreb
Journal:  Tetrahedron Lett       Date:  2010-04-14       Impact factor: 2.415

4.  Further studies of intramolecular Michael reactions of nitrosoalkenes for construction of functionalized bridged ring systems.

Authors:  Praveen Kumar; Puhui Li; Ilia Korboukh; Tony L Wang; Hemant Yennawar; Steven M Weinreb
Journal:  J Org Chem       Date:  2011-02-28       Impact factor: 4.354

5.  Copper(I)-catalyzed addition of Grignard reagents to in situ-derived N-sulfonyl azoalkenes: an umpolung alkylation procedure applicable to the formation of up to three contiguous quaternary centers.

Authors:  John M Hatcher; Don M Coltart
Journal:  J Am Chem Soc       Date:  2010-04-07       Impact factor: 15.419

6.  Catalytic asymmetric addition of thiols to nitrosoalkenes leading to chiral non-racemic α-sulfenyl ketones.

Authors:  John M Hatcher; Mark C Kohler; Don M Coltart
Journal:  Org Lett       Date:  2011-06-29       Impact factor: 6.005

7.  Investigation of the stereochemistry of intermolecular conjugate additions of nucleophiles to acyclic nitrosoalkenes.

Authors:  Jason A Witek; Steven M Weinreb
Journal:  Org Lett       Date:  2011-02-04       Impact factor: 6.005

8.  Catalytic cross-coupling of alkylzinc halides with alpha-chloroketones.

Authors:  Chrysa F Malosh; Joseph M Ready
Journal:  J Am Chem Soc       Date:  2004-08-25       Impact factor: 15.419

  8 in total
  1 in total

Review 1.  Conjugated nitrosoalkenes as Michael acceptors in carbon-carbon bond forming reactions: a review and perspective.

Authors:  Yaroslav Dmitrievich Boyko; Valentin Sergeevich Dorokhov; Alexey Yu Sukhorukov; Sema Leibovich Ioffe
Journal:  Beilstein J Org Chem       Date:  2017-10-23       Impact factor: 2.883

  1 in total

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