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Literature DB >> 17579448

Metalated nitriles: cation-controlled cyclizations.

Fraser F Fleming¹, Yunjing Wei, Wang Liu, Zhiyu Zhang.

Abstract

Judicious choice of cation allows the selective cyclization of substituted gamma-hydroxynitriles to trans- or cis-decalins and trans- or cis-bicyclo[5.4.0]undecanes. The stereoselectivities are consistent with deprotonations generating two distinctly different metalated nitriles: an internally coordinated nitrile anion with BuLi, and a C-magnesiated nitrile with i-PrMgCl. Employing cations to control the geometry of metalated nitriles permits stereodivergent cyclizations with complete control over the stereochemistry of the quaternary, nitrile-bearing carbon.

Entities: Chemical

Mesh：

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Year: 2007 PMID： 17579448 PMCID： PMC2533635 DOI： 10.1021/ol071084k

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

12 in total

1. Oxonitriles: multicomponent Grignard addition-alkylations.

Authors: Fraser F Fleming; Zhiyu Zhang; Qunzhao Wang; Omar W Steward
Journal: Angew Chem Int Ed Engl Date: 2004-02-20 Impact factor: 15.336

2. Conjugate addition of 2- and 4-pyridylcuprates: an expeditious asymmetric synthesis of natural (-)-evoninic acid.

Authors: Alan C Spivey; Lena Shukla; Judy F Hayler
Journal: Org Lett Date: 2007-02-09 Impact factor: 6.005

3. 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

4. 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

2. Isolation of the Metalated Ylides [Ph₃ P-C-CN]M (M=Li, Na, K): Influence of the Metal Ion on the Structure and Bonding Situation.

Authors: Christopher Schwarz; Lennart T Scharf; Thorsten Scherpf; Julia Weismann; Viktoria H Gessner
Journal: Chemistry Date: 2019-01-29 Impact factor: 5.236

2 in total

Metalated nitriles: cation-controlled cyclizations.

1. Oxonitriles: multicomponent Grignard addition-alkylations.

2. Conjugate addition of 2- and 4-pyridylcuprates: an expeditious asymmetric synthesis of natural (-)-evoninic acid.

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

4. 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.

5. Metalated nitriles: chelation-controlled cyclizations to cis and trans hydrindanes and decalins.

6. Metalated nitriles: organolithium, -magnesium, and -copper exchange of alpha-halonitriles.

7. Nitrile anions: solvent-dependent cyclizations.

8. Cyclic alkenenitriles: synthesis, conjugate addition, and stereoselective annulation.

9. Cyclic oxonitriles: stereodivergent grignard addition-alkylations.

10. The first enantioenriched metalated nitrile possessing macroscopic configurational stability.

1. Metalated Nitriles: Stereodivergent Cation-Controlled Cyclizations1.

2. Isolation of the Metalated Ylides [Ph₃ P-C-CN]M (M=Li, Na, K): Influence of the Metal Ion on the Structure and Bonding Situation.