ChemInform Abstract: Auxiliary Structure and Asymmetric Induction in the “Mukaiyama-Aldol” Reactions of Chiral Silyl Ketene Acetals.

ChemInform ◽  
1990 ◽  
Vol 21 (18) ◽  
Author(s):  
C. GENNARI ◽  
F. MOLINARI ◽  
P. G. COZZI ◽  
A. OLIVA
Keyword(s):  
Asymmetric Induction ◽  
Aldol Reactions ◽  
Mukaiyama Aldol ◽  
Ketene Acetals ◽  
Silyl Ketene Acetals

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

Clay Montmorillonite-Catalyzed Aldol Reactions of Silyl Ketene Acetals with Carbonyl Compounds

1987 ◽  
Vol 60 (7) ◽  
pp. 2689-2691 ◽  
Author(s):  
Makoto Onaka ◽  
Ryosuke Ohno ◽  
Motomitsu Kawai ◽  
Yusuke Izumi
Keyword(s):  
Carbonyl Compounds ◽  
Aldol Reactions ◽  
Ketene Acetals ◽  
Silyl Ketene Acetals

Stereoselective Aldol Additions of Glycolic Acid and Its Derivatives

Synthesis ◽  
2019 ◽  
Vol 51 (08) ◽  
pp. 1715-1745 ◽  
Author(s):  
Tobias Engesser ◽  
Reinhard Brückner
Keyword(s):  
Lactic Acid ◽  
Acid Derivative ◽  
Glycolic Acid ◽  
Methyl Substituent ◽  
Comprehensive Overview ◽  
Aldol Additions ◽  
Mukaiyama Aldol ◽  
Ketene Acetals ◽  
Silyl Ketene Acetals ◽  
Selection Of

This review gives a comprehensive overview of aldol additions of glycolic acid derivatives to achiral aldehydes and acetals affording α,β-dihydroxycarboxylic acids or derivatives thereof. The focus is on simple diastereoselectivity. A selection of related aldol additions is also presented: aldol additions of glycolic acid derivatives to ketones with two different substituents and aldol additions of α-substituted glycolic acid derivatives.1 Introduction1.1 Organization of this Review1.2 Outside the Scope of this Review: Aldol Additions Giving α,β-Dihydroxyaldehydes and α,β-Dihydroxyketones Diastereoselectively1.3 Non-Aldol Routes to Diastereomerically Pure α,β-Dihydroxycarboxylic Acid Derivatives2 Aldol Additions of Glycolic Acid (Derivative) Enolates to Aldehydes2.1 Aldol Additions of Glycolate Enolates (‘Glycolic Acid Dianions’)2.2 Aldol Additions of Glycolic Ester Enolates2.3 Aldol Additions of Glycolic Thioester Enolates2.4 Aldol Additions of Glycolimide Enolates2.5 Aldol Additions of Glycolamide Enolates2.6 Mukaiyama Aldol Additions of Silyl Ketene Acetals of Glycolic Esters­ and Thioesters2.7 Aldol Additions of Glycoloyl Chlorides via Acyl Ammonium Enolates3 Aldol-Providing Substitutions of Glycolimide Enolates in Acetals4 Additions Related to Aldol Additions of Glycolic Acid Derivative Enolates to Aldehydes4.1 Selected Simply Diastereoselective Aldol Additions of Enolates of Glycolic Acid Derivatives to Ketones with Two Different Substituents4.2 Simply Diastereoselective Aldol Additions of Enolates of Glycolic Acid Derivatives with a Methyl Substituent at C-α (Lactic Acid Derivatives)5 Conclusion

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