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Volumn 28, Issue 1, 1989, Pages 69-71

Asymmetric Homoaldol Reaction by Enantioselective Lithiation of a Prochiral 2‐Butenyl Carbamate

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Indexed keywords

EID: 84990165746 PISSN: 05700833 EISSN: 15213773 Source Type: Journal
DOI: 10.1002/anie.198900691 Document Type: Article

Times cited : (115)

References (35)

1
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- α-Deprotonierung eines α-chiralen 2-Alkenylcarbamats unter Retention und Lithium-Titan-Austausch unter Inversion - zur Homoaldol-Reaktion unter 1,3-Chiralitätsübertragung
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4
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- (a) Reviews
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- Hoppe, D.¹

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- Hoppe, D.¹

7
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- Hochenantioselektive Homoaldol-Addition mit chiralenN-Allylharnstoffen - Anwendung zur Synthese optisch reiner γ-Lactone
- (a) Other methods for asymmetric homoaldol reactions
- (1984) Angewandte Chemie , vol.96 , pp. 895
- Roder, H.¹ Helmchen, G.² Peters, E.‐M.³ von Schnering, H.‐G.⁴

11
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12
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- Metallierte Stickstoff-Derivate der Kohlensäure in der organischen Synthese, XXVII. – Homoaldol-Reaktion, VII. Lithiierung acyclischerN,N-Dialkylcarbamidsäure-2-alkenylester; Silylierung und γ-selektive α-Hydroxyalkylierung von Homoenolat-Reagenzien
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14
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- Enantioselektive Synthese von Methylfuranosiden unnatürlicher 3,6-Didesoxy-3-methyl-aldohexosen aus Milchsäureestern durch Homoaldol-Reaktion
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- Hoppe, D.¹ Tarara, G.² Wilckens, M.³ Jones, P.G.⁴ Schmidt, D.⁵ Stezowski, J.J.⁶

16
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- J. D. Morrison, Academic Press, New York
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- Morrison, J.D.¹

17
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- (–)‐Sparteine has already been used for chiral modification of “cations” of organometallic compounds containing achiral “carbanion” moieties: see, for example,. It is important to note that the asymmetric induction in that case is caused by the orientation of the starting materials with respect to the cation. Thus, the direction and extent of the asymmetric induction cannot be predicted. Application to a chiral Grignard compound gave only a slight enantiomeric exess (7%ee)
- (1973) Tetrahedron , vol.29 , pp. 3659
- Guetté, M.¹ Capillon, J.² Guetté, J.‐P.³

20
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- R. Scheffold, Salle, Frankfurt
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- Seebach, D.¹ Weidmann, B.²

21
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- 3]. The 1‐H signal of 6 is shifted 0.2‐0.5 ppm downfield compared with that of ent‐6.

22
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- Abschätzung der konfigurativen Stabilität chiraler Organometallreagentien
- For the problem of double stereodifferentiation in the addition of chiral organometallic compounds, see
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- Hoffmann, R.W.¹ Lanz, J.² Metternich, R.³ Tarara, G.⁴ Hoppe, D.⁵

25
- 84990119637
- 11c : [α] D20 + 52.1 (methanol, c = 1). The optical purity of 62%, determined by comparison of the optical rotation with that of the natural product [13a], is presumably incorrect, since the transformation of 6c (83% ee) cannot be accompanied by racemization. 11a (83% ee): [α] D20 + 31.8 (methanol, c = 2.5).

27
- 0040994161
- (b) enantioselective synthesis
- (1987) Tetrahedron , vol.43 , pp. 4497
- Ortuño, R.M.¹ Merce, R.² Font, J.³

28
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31
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- Stereoselektive Synthese von Bausteinen mit drei aufeinanderfolgenden stereogenen Zentren, wichtigen Vorstufen für polyketide Naturstoffe
- (a) Reviews on the use of crotylmetal compounds as propanal enolate equivalents
- (1987) Angewandte Chemie , vol.99 , pp. 503
- Hoffmann, R.W.¹

33
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- α-Chiral allylboronates: reagents for asymmetric synthesis
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- Hoffmann, R.W.¹

35
- 84990165179
- The crystallization of (R)‐2b. 7 is induced by cyclohexane. It is still not clear whether the cyclohexane is incorporated into the crystal lattice or only serves as a crystallization seed. As we have shown for 6a, after addition of cyclohexane, n‐butyllithium in hexane can also be used for the deprotonation, giving the same results.

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