Literature DB >> 24260015

Cyclic Metalated Nitriles: Stereoselective Cyclizations to cis- and trans-Hydrindanes, Decalins, and Bicyclo[4.3.0]undecanes.

Fraser F Fleming1, Subramanyham Gudipati.   

Abstract

Metalated nitriles are nucleophilic n class="Species">chameleons whose precise identity is determined by the nature of the metal, the solvent, the temperature, and the structure of the nitrile. The review surveys the different structural types and their cyclization trajectories to show how to selectively tune the metalated nitrile geometry for stereoselective cyclizations to a variety of cis or trans hydrindanes, decalins, and bicyclo[4.3.0]undecanes.

Entities:  

Keywords:  Cyclizations; Decalin; Hydrindane; Nitriles; Stereoselectivity

Year:  2008        PMID: 24260015      PMCID: PMC3831376          DOI: 10.1002/ejoc.200800715

Source DB:  PubMed          Journal:  European J Org Chem        ISSN: 1099-0690


  34 in total

1.  Intermolecular C-H insertions and cyclization reactions involving a stable germylene.

Authors:  K A Miller; T W Watson; J E Bender; M M Banaszak Holl; J W Kampf
Journal:  J Am Chem Soc       Date:  2001-02-07       Impact factor: 15.419

2.  Progress toward the total synthesis of kalihinane diterpenoids.

Authors:  R D White; J L Wood
Journal:  Org Lett       Date:  2001-06-14       Impact factor: 6.005

3.  beta-Siloxy unsaturated nitriles: stereoselective cyclizations to cis- and trans-decalins.

Authors:  F F Fleming; B C Shook; T Jiang; O W Steward
Journal:  Org Lett       Date:  1999-11-18       Impact factor: 6.005

4.  Total synthesis of (+/-)-scopadulin.

Authors:  S M Rahman; H Ohno; T Murata; H Yoshino; N Satoh; K Murakami; D Patra; C Iwata; N Maezaki; T Tanaka
Journal:  J Org Chem       Date:  2001-07-13       Impact factor: 4.354

5.  Asymmetric synthesis of the protoberberine alkaloid (S)-(-)-xylopinine using enantiopure sulfinimines.

Authors:  Franklin A Davis; Pradyumna K Mohanty
Journal:  J Org Chem       Date:  2002-02-22       Impact factor: 4.354

6.  Sulfinimine-mediated asymmetric synthesis of 1,3-disubstituted tetrahydroisoquinolines: a stereoselective synthesis of cis- and trans-6,8-dimethoxy-1,3-dimethyl-1,2,3,4-tetrahydroisoquinoline.

Authors:  F A Davis; P K Mohanty; D M Burns; Y W Andemichael
Journal:  Org Lett       Date:  2000-11-30       Impact factor: 6.005

7.  A formal total synthesis of the sesterterpenoid (+/-)-dysidiolide and approaches to the syntheses of (+/-)-6-epi-, (+/-)-15-epi-, and (+/-)-6,15-bisepidysidiolide.

Authors:  E Piers; S Caillé; G Chen
Journal:  Org Lett       Date:  2000-08-10       Impact factor: 6.005

8.  Unsaturated nitriles: stereoselective MgO eliminations.

Authors:  Fraser F Fleming; Brian C Shook
Journal:  J Org Chem       Date:  2002-05-31       Impact factor: 4.354

9.  The first total synthesis of (+/-)-scopadulin, an antiviral aphidicolane diterpene.

Authors:  S M Rahman; H Ohno; T Murata; H Yoshino; N Satoh; K Murakami; D Patra; C Iwata; N Maezaki; T Tanaka
Journal:  Org Lett       Date:  2001-02-22       Impact factor: 6.005

10.  Nitrile anions: solvent-dependent cyclizations.

Authors:  Fraser F Fleming; Brian C Shook
Journal:  J Org Chem       Date:  2002-05-03       Impact factor: 4.354

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