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1
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0002131970
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Enantiomerenreine tertiäre Alkohole durch TADDOL-vermittelte Additionen an Ketone - oder wie man ein Grignard-Reagens enantioselektiv macht
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Preliminary Communication
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(1992)
Angewandte Chemie
, vol.104
, pp. 96-97
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Weber1
Seebach2
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3
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84912999937
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Reactions from which one of the two possible enantiomeric forms of a product is obtained preferentially.
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6
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0027396039
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See the general introduction of a recent paper, (Tetrahedron Symposia-in-Print Number 49 “Synthesis of Optically Active Compounds - Prospects for the 21st Century”).
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(1993)
Tetrahedron
, vol.49
, pp. 1711-1724
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Seebach1
Hayakawa2
Sakaki3
Schweizer4
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15
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46049093325
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Enantioselektive 1,2-Additionen von Li-, Mg-, Zn- und Cu-organischen Verbindungen und von Li-Enolaten an Carbonylverbindungen im chiralen Medium DDB
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(1979)
Helvetica Chimica Acta
, vol.62
, pp. 1701-1709
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Seebach1
Langer2
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20
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0001956304
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Enantioselektive Addition von Organometallreagentien an Carbonylverbindungen: Übertragung, Vervielfältigung und Verstärkung der Chiralität
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Review article
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(1991)
Angewandte Chemie
, vol.103
, pp. 34-55
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Noyori1
Kitamura2
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27
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0010342137
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Enantioselektive katalytische Addition funktionalisierter Dialkylzinkverbindungen an β-stannylierte Aldehyde; eine einfache Methode zur Herstellung nichtracemischer β- und γ-funktionalisierter sekundärer Alkohole
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(1993)
Angewandte Chemie
, vol.105
, pp. 629-631
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Brieden1
Ostwald2
Knochel3
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29
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0002098511
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Katalytische und stöchiometrische enantioselektive Additionen von Diethylzink an Aldehyde mit Hilfe eines neuartigen chiralen Spirotitanats
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(1991)
Angewandte Chemie
, vol.103
, pp. 100-101
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Schmidt1
Seebach2
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31
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0000968031
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Titanat-katalysierte enantioselektive Addition vonin situ aus Grignard-Reagentien in Ether erzeugten Alkylzinkverbindungen an Aldehyde
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(1991)
Angewandte Chemie
, vol.103
, pp. 991-992
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Seebach1
Behrendt2
Felix3
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34
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0000233048
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2,2-Dimethyl-α,α,α′,α′-tetra(naphth-2-yl)-1,3-dioxolan-4,5-dimethanol (DINOL) für die Titanat-vermittelte, enantioselektive Addition von Diethylzink an Aldehyde
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The following papers describe the, so far, most general method for the addition of primary alkyl Zn reagents to non-functionalized aliphatic, α,β-unsaturated (CC and CC), aromatic and heteroaromatic aldehydes with formation of secondary alcohols of ≥97% ee, using the Ti-TADDOLate from 1b:
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(1991)
Angewandte Chemie
, vol.103
, pp. 1383-1385
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Schmidt1
Seebach2
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35
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33748215418
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D. Seebach, B. Schmidt, Y.-M. Wang, A.K. Beck, Tetrahedron, (Tetrahedron Symposia-in-Print “Recent Aspects of Catalytic Asymmetric Addition Reactions”), in preparation.
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(1991)
Angew. Chem. Int. Ed. Engl.
, vol.30
, pp. 1321-1323
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Schmidt1
Seebach2
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36
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0000389195
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On the Mechanisms of Enantioselective Reactions Using ?,?,??,?? -Tetraaryl-1,3-dioxolane-4,5-dimethanol(TADDOL)-Derived Titanates: Differences betweenC2- andC1-symmetrical TADDOLs - facts, implications and generalizations
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Mechanism
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(1992)
Helvetica Chimica Acta
, vol.75
, pp. 2171-2209
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Seebach1
Plattner2
Beck3
Wang4
Hunziker5
Petter6
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40
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84913004693
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2 to dimethyl citraconate and GC comparison with authentic samples of (R)- and (S)-dimethyl citraconate.
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44
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84913001225
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2Zn to aldehydes referred to above [19].
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45
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84913002505
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The α-heteroatom in 2-furyl- and 2-pyridyl methyl ketone seems to interfere with the reaction as well, see 15 and 20, but also 13!
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47
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84912985820
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The N-tosyl-imine of benzaldehyde gave totally racemic product with EtMgBr in the presence of Mg-TADDOLate.
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51
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84913007996
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Reduction of the ketones by the Grignard reagents was observed only occasionally.
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54
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0000374154
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A detailed description of the mechanism of reaction of Grignard reagents with ketones
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(1980)
Pure and Applied Chemistry
, vol.52
, pp. 545-569
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Ashby1
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59
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0001269629
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Struktur und Reaktivität von Lithiumenolaten, vom Pinakolon zur selektivenC-Alkylierung von Peptiden – Schwierigkeiten und Möglichkeiten durch komplexe Strukturen
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For crystal structures of organomagnesium derivatives see [35], Fig. 6 in [4a], Fig. 17 in
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(1988)
Angewandte Chemie
, vol.100
, pp. 1685-1715
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Seebach1
Seebach2
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60
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84990085779
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Structure and Reactivity of Lithium Enolates. From Pinacolone to SelectiveC-Alkylations of Peptides. Difficulties and Opportunities Afforded by Complex Structures
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(1988)
Angewandte Chemie International Edition in English
, vol.27
, pp. 01624-1654
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62
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84913008309
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♯ between the competing transition states of ca. 1.6 kcal/mol.
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65
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0001708429
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For a description of a low-temperature apparatus see
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(1983)
Chimia
, vol.37
, pp. 449-462
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Seebach1
Hidber2
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