Prev. Article Next Article Table of Contents

Review

1,n-Dicarbanionic Titanium Intermediates from Monocarbanionic Organometallics and Their Application in Organic Synthesis

Figures
Citing Articles

Your current credentials do not allow retrieval of the full text.

Purchase the full-text

PDF/HTML,
figures/images,
references and tables,
(where available)

Oleg G. Kulinkovich* and Armin de Meijere*

Chemical Department of Belarussian State University, Skaryny Av. 4, 220050 Minsk, Belarus, and Institut für Organische Chemie der Georg-August-Universität Göttingen, Tammannstrasse 2, D-37077 Göttingen, Germany

Chem. Rev., 2000, 100 (8), pp 2789–2834

DOI: 10.1021/cr980046z

Publication Date (Web): July 21, 2000

Section:

Organometallic and Organometalloidal Compounds

I. Introduction
II. 1,1-Dicarbanionic Equivalents
- A. Organoaluminum Precursors
- B. Organolithium and Organomagnesium Precursors
III. Generation of 1,2-Dicarbanionic Equivalents
- A. Organomagnesium Precursors
- B. Ligand Exchange with Alkenes
- C. Ligand Exchange with Alkynes
IV. Interconversion of Dicarbanionic Equivalents
- A. 1,3-Dicarbanionic Equivalents
- B. Interconversion of 1,2- and 1,4-Dicarbanionic Equivalents
V. Applications in Natural Product Syntheses
- A. 1,1-Dicarbanionic Equivalents
- B. 1,2-Dicarbanionic Equivalents
- C. 1,4-Dicarbanionic Equivalents
VI. Conclusion
VII. Acknowledgments
VIII. References

View: Full Text HTML | Hi-Res PDF | PDF w/ Links

Citing Articles

View all 154 citing articles

Citation data is made available by participants in CrossRef's Cited-by Linking service. For a more comprehensive list of citations to this article, users are encouraged to perform a search in SciFinder.

This article has been cited by 81 ACS Journal articles (5 most recent appear below).

Multikilogram-Scale Synthesis of a Chiral Cyclopropanol and an Investigation of the Safe Use of Lithium Acetylide–Ethylene Diamine Complex
Ephraim M. Bassan, Carl A. Baxter, Gregory L. Beutner, Khateeta M. Emerson, Fred J. Fleitz, Simon Johnson, Stephen Keen, Mary M. Kim, Jeffrey T. Kuethe, William R. Leonard, Peter R. Mullens, Daniel J. Muzzio, Christopher Roberge, and Nobuyoshi Yasuda
Organic Process Research & Development2012 16 (1), 87-95
- Multikilogram-Scale Synthesis of a Chiral Cyclopropanol and an Investigation of the Safe Use of Lithium Acetylide–Ethylene Diamine Complex
  Ephraim M. Bassan, Carl A. Baxter, Gregory L. Beutner, Khateeta M. Emerson, Fred J. Fleitz, Simon Johnson, Stephen Keen, Mary M. Kim, Jeffrey T. Kuethe, William R. Leonard, Peter R. Mullens, Daniel J. Muzzio, Christopher Roberge, and Nobuyoshi Yasuda
  Organic Process Research & Development2012 16 (1), 87-95
  A six-step route starting from a readily available vinyl boronate was identified to produce an enantioenriched cyclopropanol in an overall 16% yield. Key steps involve the use of lithium acetylide-ethylene diamine complex 5 and an enzymatic resolution of ...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
Total Synthesis of (−)-Virginiamycin M₂: Application of Crotylsilanes Accessed by Enantioselective Rh(II) or Cu(I) Promoted Carbenoid Si–H Insertion
Jie Wu and James S. Panek
The Journal of Organic Chemistry2011 76 (24), 9900-9918
- Total Synthesis of (−)-Virginiamycin M₂: Application of Crotylsilanes Accessed by Enantioselective Rh(II) or Cu(I) Promoted Carbenoid Si–H Insertion
  Jie Wu and James S. Panek
  The Journal of Organic Chemistry2011 76 (24), 9900-9918
  A stereoselective synthesis of the antibiotic (−)-virginiamycin M2 is detailed. A convergent strategy was utilized that proceeded in 10 steps (longest linear sequence) from enantioenriched silane (S)-15. This reagent, which was prepared via a Rh(II)- or ...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
Active Low-Valent Niobium Catalysts from NbCl₅ and Hydrosilanes for Selective Intermolecular Cycloadditions
Yasushi Satoh and Yasushi Obora
The Journal of Organic Chemistry2011 76 (20), 8569-8573
- Active Low-Valent Niobium Catalysts from NbCl₅ and Hydrosilanes for Selective Intermolecular Cycloadditions
  Yasushi Satoh and Yasushi Obora
  The Journal of Organic Chemistry2011 76 (20), 8569-8573
  An active niobium catalyst was developed via a simple and nontoxic reduction method from NbCl5/hydrosilane and utilized for the selective [2 + 2 + 2] cycloaddition reaction of terminal alkynes and alkenes/α,ω-dienes, to give 1,3-cyclohexadiene derivatives ...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
Density Functional Theory Study of the Mechanism and Origins of Stereoselectivity in the Asymmetric Simmons–Smith Cyclopropanation with Charette Chiral Dioxaborolane Ligand
Tao Wang, Yong Liang, and Zhi-Xiang Yu
Journal of the American Chemical Society2011 Article ASAP
- Density Functional Theory Study of the Mechanism and Origins of Stereoselectivity in the Asymmetric Simmons–Smith Cyclopropanation with Charette Chiral Dioxaborolane Ligand
  Tao Wang, Yong Liang, and Zhi-Xiang Yu
  Journal of the American Chemical Society2011 Article ASAP
  Asymmetric Simmons–Smith reaction using Charette chiral dioxaborolane ligand is a widely applied method for the construction of enantiomerically enriched cyclopropanes. The detailed mechanism and the origins of stereoselectivity of this important reaction ...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
Ti(O-i-Pr)₄/Me₃SiCl/Mg-Mediated Reductive Cleavage of Sulfonamides and Sulfonates to Amines and Alcohols
Noriaki Shohji, Tsuyoshi Kawaji, and Sentaro Okamoto
Organic Letters2011 Article ASAP
- Ti(O-i-Pr)₄/Me₃SiCl/Mg-Mediated Reductive Cleavage of Sulfonamides and Sulfonates to Amines and Alcohols
  Noriaki Shohji, Tsuyoshi Kawaji, and Sentaro Okamoto
  Organic Letters2011 Article ASAP
  A low-valent titanium generated in situ from Ti(O-i-Pr)4, Me3SiCl, and Mg powder in THF reacted with aryl- and alkyl-sulfonamides of aryl and alkyl amines in a reductive N–S/S–O/S–C bond cleaving pathway to provide the corresponding amines and ...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links

Tools

SciFinder Links

Explore by:

Author of this Article Any Author Research Topic

History

Published In Issue August 09, 2000
Received March 21, 2000

Select a CAS section from the 5 main topical divisions below:

Review

1,n-Dicarbanionic Titanium Intermediates from Monocarbanionic Organometallics and Their Application in Organic Synthesis

Table of Contents

Citing Articles

Multikilogram-Scale Synthesis of a Chiral Cyclopropanol and an Investigation of the Safe Use of Lithium Acetylide–Ethylene Diamine Complex

Multikilogram-Scale Synthesis of a Chiral Cyclopropanol and an Investigation of the Safe Use of Lithium Acetylide–Ethylene Diamine Complex

Total Synthesis of (−)-Virginiamycin M₂: Application of Crotylsilanes Accessed by Enantioselective Rh(II) or Cu(I) Promoted Carbenoid Si–H Insertion

Total Synthesis of (−)-Virginiamycin M₂: Application of Crotylsilanes Accessed by Enantioselective Rh(II) or Cu(I) Promoted Carbenoid Si–H Insertion

Active Low-Valent Niobium Catalysts from NbCl₅ and Hydrosilanes for Selective Intermolecular Cycloadditions

Active Low-Valent Niobium Catalysts from NbCl₅ and Hydrosilanes for Selective Intermolecular Cycloadditions

Density Functional Theory Study of the Mechanism and Origins of Stereoselectivity in the Asymmetric Simmons–Smith Cyclopropanation with Charette Chiral Dioxaborolane Ligand

Density Functional Theory Study of the Mechanism and Origins of Stereoselectivity in the Asymmetric Simmons–Smith Cyclopropanation with Charette Chiral Dioxaborolane Ligand

Ti(O-i-Pr)₄/Me₃SiCl/Mg-Mediated Reductive Cleavage of Sulfonamides and Sulfonates to Amines and Alcohols