Double diastereodifferentiation in the Mukaiyama aldol reactions of π-allyltricarbonyliron lactone complexes: 1,7- vs. 1,2-asymmetric induction

1998 ◽  
pp. 3349-3354 ◽  
Author(s):  
Steven V. Ley ◽  
Liam R. Cox ◽  
Julia M. Worrall
Keyword(s):  
Asymmetric Induction ◽  
Aldol Reactions ◽  
Mukaiyama Aldol

Auxiliary structure and asymmetric induction in the “Mukaiyama-aldol” reactions of chiral silyl ketene acetals

1989 ◽  
Vol 30 (38) ◽  
pp. 5163-5166 ◽  
Author(s):  
Cesare Gennari ◽  
Francesco Molinari ◽  
PierGiorgio Cozzi ◽  
Ambrogio Oliva
Keyword(s):  
Asymmetric Induction ◽  
Aldol Reactions ◽  
Mukaiyama Aldol ◽  
Ketene Acetals ◽  
Silyl Ketene Acetals

scholarly journals Syn-selective silicon Mukaiyama-type aldol reactions of (pentafluoro-λ6-sulfanyl)acetic acid esters with aldehydes

2018 ◽  
Vol 14 ◽  
pp. 373-380 ◽  
Author(s):  
Anna-Lena Dreier ◽  
Andrej V Matsnev ◽  
Joseph S Thrasher ◽  
Günter Haufe
Keyword(s):  
Acetic Acid ◽  
Aldol Condensation ◽  
Aldol Reactions ◽  
Complex Structures ◽  
Bond Forming ◽  
Hydroxyalkanoic Acid ◽  
Mukaiyama Aldol ◽  
Substituted Benzaldehydes ◽  
Acetic Acid Esters ◽  
Acid Esters

Aldol reactions belong to the most frequently used C–C bond forming transformations utilized particularly for the construction of complex structures. The selectivity of these reactions depends on the geometry of the intermediate enolates. Here, we have reacted octyl pentafluoro-λ6-sulfanylacetate with substituted benzaldehydes and acetaldehyde under the conditions of the silicon-mediated Mukaiyama aldol reaction. The transformations proceeded with high diastereoselectivity. In case of benzaldehydes with electron-withdrawing substituents in the para-position, syn-α-SF5-β-hydroxyalkanoic acid esters were produced. The reaction was also successful with meta-substituted benzaldehydes and o-fluorobenzaldehyde. In contrast, p-methyl-, p-methoxy-, and p-ethoxybenzaldehydes led selectively to aldol condensation products with (E)-configured double bonds in 30–40% yields. In preliminary experiments with an SF5-substituted acetic acid morpholide and p-nitrobenzaldehyde, a low amount of an aldol product was formed under similar conditions.

ChemInform Abstract: Uncatalyzed, Diastereoselective Vinylogous Mukaiyama Aldol Reactions on Aqueous Media: Pyrrole vs Furan 2-Silyloxy Dienes.

ChemInform ◽  
2011 ◽  
Vol 42 (14) ◽  
pp. no-no
Author(s):  
Claudio Curti ◽  
Lucia Battistini ◽  
Franca Zanardi ◽  
Gloria Rassu ◽  
Vincenzo Zambrano ◽  
...  
Keyword(s):  
Aqueous Media ◽  
Aldol Reactions ◽  
Mukaiyama Aldol
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