α-Metallated O-2-Alkenyl Carbamates: Synthetic Equivalents
of Chiral Homoenolates and Materials for Asymmetric Homoaldol
Reaction

Dieter Hoppe

doi:10.1055/s-0028-1083280

PAPER

α-Metallated O-2-Alkenyl Carbamates: Synthetic Equivalents of Chiral Homoenolates and Materials for Asymmetric Homoaldol Reaction

Dieter Hoppe*
Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstraße 40, 48149 Münster, Germany
Fax: +49(251)8339772; e-Mail: dhoppe@uni-muenster.de ;

Abstract

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Abstract

The review article provides a personal overview on the development and application in enantioselective synthesis of nonracemic chiral homoenolate reagents, based on allylic N,N-dialkylcarbamates and the ideas behind it. Further, the impact of these results, concerning stereoselective deprotonation, mainly under the influence of the chiral diamine (-)-sparteine, for the generation of a wide range of chiral building blocks is briefly presented.

Key words

asymmetric synthesis - homoenolates - stereoselective deprotonation - chiral carbanions - (-)-sparteine

Full Text

References

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<A NAME="RC05608SS-75">75</A> Beckmann E. Hoppe D. Synthesis 2005, 217

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<A NAME="RC05608SS-77">77</A> Stynmiest JL. Dutheuil G. Mahmood A. Aggarwal VK. Angew. Chem. Int. Ed. 2007, 46: 7491 ; Angew. Chem. 2007, 119, 7635

<A NAME="RC05608SS-78A">78a</A> Deiters A. Hoppe D. Angew. Chem. Int. Ed. 1999, 38: 546 ; Angew. Chem. 1999, 111, 529

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<A NAME="RC05608SS-80B">80b</A> Deiters A. Mück-Lichtenfeld C. Fröhlich R. Hoppe D. Chem. Eur. J. 2002, 8: 1833

<A NAME="RC05608SS-81">81</A> Deiters A. Wibbeling B. Hoppe D. Adv. Synth. Catal. 2001, 343: 181

<A NAME="RC05608SS-82A">82a</A> Martínez MM. Hoppe D. Org. Lett. 2004, 6: 3743

<A NAME="RC05608SS-82B">82b</A> Martínez MM. Hoppe D. Eur. J. Org. Chem. 2005, 1427

<A NAME="RC05608SS-83">83</A> Seppi M. Kalkofen R. Reupohl J. Fröhlich R. Hoppe D. Angew. Chem. Int. Ed. 2004, 43: 1423 ; Angew. Chem. 2004, 116, 1447

<A NAME="RC05608SS-84">84</A> Würthwein E.-U. Hoppe D. J. Org. Chem. 2008, 73: 9055

<A NAME="RC05608SS-85">85</A> Reuber J. Fröhlich R. Hoppe D. Org. Lett. 2004, 6: 783

<A NAME="RC05608SS-86">86</A> Bou Chedid R. Brümmer M. Wibbeling B. Fröhlich R. Hoppe D. Angew. Chem. Int. Ed. 2007, 46: 3131 ; Angew. Chem. 2007, 119, 3192

<A NAME="RC05608SS-87">87</A> Bou Chedid R. Fröhlich R. Wibbeling B. Hoppe D. Eur. J. Org. Chem. 2007, 3179

<A NAME="RC05608SS-88">88</A> Reuber J. Fröhlich R. Hoppe D. Eur. J. Org. Chem. 2005, 3017

<A NAME="RC05608SS-89A">89a</A> Kalkofen R. Brandau S. Wibbeling B. Hoppe D. Angew. Chem. Int. Ed. 2004, 43: 6667 ; Angew. Chem. 2004, 116, 6836

<A NAME="RC05608SS-89B">89b</A> Kalkofen R. Brandau S. Ünaldi S. Fröhlich R. Hoppe D. Eur. J. Org. Chem. 2005, 4571

<A NAME="RC05608SS-90">90</A> Risatti CA. Taylor RE. Angew. Chem. Int. Ed. 2004, 34: 6671 ; Angew. Chem. 2004, 116, 6839

<A NAME="RC05608SS-91">91</A> Taylor RE. Risatti CA. Engelhardt FC. Schmitt MJ. Org. Lett. 2003, 5: 1377

<A NAME="RC05608SS-92A">92a</A> Matteson AE. Bharadwaj AR. Scheidt KA. J. Am. Chem. Soc. 2004, 126: 2314

<A NAME="RC05608SS-92B">92b</A> Phillips EN. Reynolds TE. Scheidt KA. J. Am. Chem. Soc. 2008, 130: 2416

<A NAME="RC05608SS-92C">92c</A> Chan A. Scheidt KA. J. Am. Chem. Soc. 2008, 130: 2740

<A NAME="RC05608SS-93">93</A> Sohn SS. Rosen EL. Bode JW. J. Am. Chem. Soc. 2004, 126: 14370

<A NAME="RC05608SS-94">94</A> Burstein C. Glorius F. Angew. Chem. Int. Ed. 2004, 43: 6205 ; Angew. Chem. 2004, 116, 6331

<A NAME="RC05608SS-95A">95a</A> Nair V. Vellalath S. Poonoth M. Suresh E. J. Am. Chem. Soc. 2006, 128: 8736

<A NAME="RC05608SS-95B">95b</A> Review: Nair V. Vellalath S. Babu B. P. Chem. Soc. Rev. 2008, 37: 2691

Selected more recent reviews:

<A NAME="RC05608SS-96A">96a</A> Hoppe D. Hense T. Angew. Chem., Int. Ed. Engl. 1997, 36: 2282 ; Angew. Chem. 1997, 109, 2376

<A NAME="RC05608SS-96B">96b</A> Hoppe D. Marr F. Brüggemann M. In Organolithiums in Enantioselective Synthesis, Topics in Organometallic Chemistry Vol. 5: Hodgson DM. Springer; Berlin / Heidelberg: 2003. p.61

<A NAME="RC05608SS-96C">96c</A> Hoppe D. Christoph G. In The Chemistry of Organolithium Compounds Rappoport Z. Marek I. Wiley; Chichester: 2004. Chap. 17. p.1055

<A NAME="RC05608SS-96D">96d</A> Hodgson DM. Gras E. Synthesis 2002, 1625

<A NAME="RC05608SS-96E">96e</A> Beak P. Johnson TA. Kim DD. Lim SH. In Organolithiums in Enantio-selective Synthesis, Topics in Organometallic Chemistry Vol. 5: Hodgson DM. Springer; Berlin/Heidelberg: 2003. p.139

<A NAME="RC05608SS-96F">96f</A> Toru T. Nakamura S. In Organolithiums in Enantioselective Synthesis, Topics in Organometallic Chemistry Vol. 5: Hodgson DM. Springer; Berlin/Heidelberg: 2003. p.177

<A NAME="RC05608SS-96G">96g</A> Hodgson DM. Tomoooka K. Gras E. In Organolithiums in Enantio-selective Synthesis, Topics in Organometallic Chemistry Vol. 5: Hodgson DM. Springer; Berlin/Heidelberg: 2003. p.217

<A NAME="RC05608SS-96H">96h</A> Clayden J. In Organolithiums in Enantio-selective Synthesis, Topics in Organometallic Chemistry Vol. 5: Springer; Berlin/Heidelberg: 2003. p.251

<A NAME="RC05608SS-96I">96i</A> Normant JF. In Organolithiums in Enantioselective Synthesis, Topics in Organometallic Chemistry Vol. 5: Springer; Berlin/Heidelberg: 2003. p.287

<A NAME="RC05608SS-96J">96j</A> Beak P. Basu A. Gallagher DJ. Park YS. Thayumanavan S. Acc. Chem. Res. 1996, 29: 552

<A NAME="RC05608SS-97A">97a</A> Carstens A. Hoppe D. Tetrahedron 1994, 50: 6097

<A NAME="RC05608SS-97B">97b</A> Hoppe D. Carstens A. Krämer T. Angew. Chem., Int. Ed. Engl. 1990, 29: 1424 ; Angew. Chem. 1990, 102, 1455

<A NAME="RC05608SS-97C">97c</A> Derwing C. Hoppe D. Synthesis 1996, 149

<A NAME="RC05608SS-98">98</A> Retzow S. Ph.D. Thesis University of Kiel; Germany: 1993.

<A NAME="RC05608SS-99A">99a</A> Hoppe D. Gonschorrek C. Tetrahedron Lett. 1987, 28: 785

<A NAME="RC05608SS-99B">99b</A> Schultz-Fademrecht C. Wibbeling B. Fröhlich R. Hoppe D. Org. Lett. 2001, 3: 1221

<A NAME="RC05608SS-99C">99c</A> Dreller S. Dyrbusch M. Hoppe D. Synlett 1991, 397

<A NAME="RC05608SS-100">100</A> Hintze F. Hoppe D. Synthesis 1992, 1216

<A NAME="RC05608SS-101">101</A> For investigations of the CH-acidity, see: Monje P. Grana P. Paleo MR. Sardina FJ. Chem. Eur. J. 2007, 13: 2277

<A NAME="RC05608SS-102A">102a</A> Schwerdtfeger J. Hoppe D. Angew. Chem. Int. Ed. Engl. 1992, 31: 1505 ; Angew. Chem. 1992, 104, 1547

<A NAME="RC05608SS-102B">102b</A> Schwerdtfeger J. Kolczewski S. Weber B. Fröhlich R. Hoppe D. Synthesis 1999, 1573

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<A NAME="RC05608SS-104A">104a</A> Hoppe D. Paetow M. Hintze F. Angew. Chem., Int. Ed. Engl. 1993, 32: 394 ; Angew. Chem. 1993, 105, 430

<A NAME="RC05608SS-104B">104b</A> Commentary:Chem. Eng. News 1993, 71 (Apr 5): 26

<A NAME="RC05608SS-105A">105a</A> Paetow M. Ahrens H. Hoppe D. Tetrahedron Lett. 1992, 33: 5323

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