Prev. Article Next Article Table of Contents

Note

Highly Stereoselective TiCl₄-Mediated Aldol Reactions from (S)-2-Benzyloxy-3-pentanone

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

Purchase the full-text

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

Victor Rodríguez-Cisterna, Cristina Villar, Pedro Romea,* and Fèlix Urpí*

Departament de Química Orgànica, Universitat de Barcelona, Martí i Franqués 1-11, 08028 Barcelona, Catalonia, Spain felix.urpi@ub.edu; pedro.romea@ub.edu

J. Org. Chem., 2007, 72 (17), pp 6631–6633

DOI: 10.1021/jo071048z

Publication Date (Web): July 18, 2007

Section:

Aliphatic Compounds

Abstract

Stereoselectivity of TiCl₄-mediated aldol reactions from (S)-2-benzyloxy-3-pentanone is dramatically improved when the reaction is carried out in the presence of 1.1 equiv of tetrahydrofuran (THF) or 1,2-dimethoxyethane (DME). The resultant 2,4-syn-4,5-syn adducts are then obtained in diastereomeric ratios up to 97:3, which proves that the appropriate choice of the Lewis acid (TiCl₄−THF or DME vs Ti(i-PrO)Cl₃) engaged in the process permits access to both syn-aldol adducts.

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

Citing Articles

View all 9 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 3 ACS Journal articles (3 most recent appear below).

C−N Bond-Forming Self-Condensation of Amide Promoted by MoCl₅ at Room Temperature
Sara Dolci, Fabio Marchetti, Guido Pampaloni, and Stefano Zacchini
Inorganic Chemistry2011 50 (9), 3846-3848
- C−N Bond-Forming Self-Condensation of Amide Promoted by MoCl₅ at Room Temperature
  Sara Dolci, Fabio Marchetti, Guido Pampaloni, and Stefano Zacchini
  Inorganic Chemistry2011 50 (9), 3846-3848
  The acylamidinium complex MoOCl4[MeC(O)N(Ph)C(Me)═NHPh] (2) was obtained by selective self-condensation of MeC(O)NHPh promoted by MoCl5. Otherwise, the stable chloroiminium salt [MoOCl4{HC(O)NMe2}][CH(Cl)═NMe2] (3) was isolated from HC(O)NMe2/MoCl5.
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
Structures and Unusual Rearrangements of Coordination Adducts of MX₅ (M = Nb, Ta; X = F, Cl) with Simple Diethers. A Crystallographic, Spectroscopic, and Computational Study
Riccardo Bini, Cinzia Chiappe, Fabio Marchetti, Guido Pampaloni and Stefano Zacchini
Inorganic Chemistry2010 49 (1), 339-351
- Structures and Unusual Rearrangements of Coordination Adducts of MX₅ (M = Nb, Ta; X = F, Cl) with Simple Diethers. A Crystallographic, Spectroscopic, and Computational Study
  Riccardo Bini, Cinzia Chiappe, Fabio Marchetti, Guido Pampaloni and Stefano Zacchini
  Inorganic Chemistry2010 49 (1), 339-351
  High-yield reactions of the pentafluoride complexes MF5 (M = Nb, Ta) with a variety of diethers, ROCH2CH(R′)OR′′, afford the ionic derivatives [MF4{κ2-ROCH2CH(R′)OR′′}2][MF6] (2a−2e) or [MF4{ROCH2CH(R′)OR′′}2][M2F11] (3a−3f) according to the metal/diether ...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
Stereoselective Synthesis of Highly Functionalized Structures from Lactate-Derived Halo Ketones
Joaquim Nebot, Pedro Romea and Fèlix Urpí
The Journal of Organic Chemistry2009 74 (19), 7518-7521
- Stereoselective Synthesis of Highly Functionalized Structures from Lactate-Derived Halo Ketones
  Joaquim Nebot, Pedro Romea and Fèlix Urpí
  The Journal of Organic Chemistry2009 74 (19), 7518-7521
  Highly diastereoselective (i-PrO)2TiCl2-mediated aldol reactions from lactate-derived α′-halo α-silyloxy ketones and subsequent treatment of the resultant aldols with a wide range of nucleophiles furnishes highly functionalized arrangements useful in ...
  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 17, 2007
Received May 23, 2007

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

Note

Highly Stereoselective TiCl₄-Mediated Aldol Reactions from (S)-2-Benzyloxy-3-pentanone

Abstract

Citing Articles

C−N Bond-Forming Self-Condensation of Amide Promoted by MoCl₅ at Room Temperature

C−N Bond-Forming Self-Condensation of Amide Promoted by MoCl₅ at Room Temperature

Structures and Unusual Rearrangements of Coordination Adducts of MX₅ (M = Nb, Ta; X = F, Cl) with Simple Diethers. A Crystallographic, Spectroscopic, and Computational Study

Structures and Unusual Rearrangements of Coordination Adducts of MX₅ (M = Nb, Ta; X = F, Cl) with Simple Diethers. A Crystallographic, Spectroscopic, and Computational Study

Stereoselective Synthesis of Highly Functionalized Structures from Lactate-Derived Halo Ketones