Highly Enantioenriched Homoenolate Reagents by Asymmetric γ-Deprotonation of Achiral 1-Silyl-Substituted 1-Alkenyl Carbamates

Author:

Reuber Jenny1,Fröhlich Roland1,Hoppe Dieter1

Affiliation:

1. Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstrasse 40, 48149 Münster, Germany

Publisher

American Chemical Society (ACS)

Subject

Organic Chemistry,Physical and Theoretical Chemistry,Biochemistry

Reference17 articles.

1. Reviews:  (a) Hoppe, D.; Hense, T.Angew. Chem.1997,109, 2376;Angew.Chem., Int. Ed. Engl.1997,36, 2282. (b) Hoppe, D.; Marr, F.; Brüggemann, M. InOrganolithium in Enantioselective Synthesis; Hodgson, D. M., Ed.; Topics in Organometallic Chemistry; Springer-Verlag:  Berlin, 2003; Vol. 5, p 61. (c) Beak, P.; Johnson, T. A.; Kim, D. D.; Lim, S. H. InOrganolithium inEnantioselective Synthesis; Hodgson, D. M., Ed.; Topics in Organometallic Chemistry; Springer-Verlag:  Berlin, 2003; Vol. 5, p 134. (d) Ahlbrecht, H.; Beyer, U.Synthesis1999, 365.

2. Asymmetrische Homoaldol-Reaktion durch enantioselektive Lithiierung eines prochiralen 2-Butenylcarbamats

3. Sparteine complexes of lithiated primary O-2-alkenyl carbamates stereochemistry of the lithium-titanium exchange and application for the synthesis of enantiomerically enriched γ-lactones

4. α-Deprotonierung eines α-chiralen 2-Alkenylcarbamats unter Retention und Lithium-Titan-Austausch unter Inversion - zur Homoaldol-Reaktion unter 1,3-Chiralitätsübertragung

5. α-Lithiation of N-(tert-Butoxycarbonyl)-N-(p- methoxyphenyl)allylamines Mediated by (−)-Sparteine:  Enantioselective Syntheses of Either Enantiomer of 3-Substituted Enecarbamates

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