Concepedia

The Influence of a β-Electron Withdrawing Substituent in Aldol Reactions of Methylketone Boron Enolates

Luiz C. Dias, Anderson A. de Marchi, Marco A. B. Ferreira, Andrea M. Aguilar

Organic Letters · 2007 · 22 citations · 32 references

DOI

Concepts

Abstract

We wish to describe here that good levels of substrate-based, 1,5-syn-stereocontrol could be achieved in the boron-mediated aldol reactions of beta-trichloromethyl methylketones with achiral aldehydes, independent of the nature of the beta-alkoxy protecting group.

References

32

Stereochemistry of alternating polyol chains: 13C NMR analysis of 1,3-diol acetonides

Scott D. Rychnovsky, Donald J. Skalitzky · Tetrahedron Letters · 1990 · 478 citations

, , +7

13C NMR chemical shift correlations in 1,3-diol acetonides. Implications for the stereochemical assignment of propionate-derived polyols

David A. Evans, Dale L. Rieger, James R. Gage · Tetrahedron Letters · 1990 · 306 citations

, , +6

Structural, mechanistic, and theoretical aspects of chelation-controlled carbonyl addition reactions

Manfred T. Reetz · Accounts of Chemical Research · 1993 · 224 citations

, , +13

Structure and basicity of silyl ethers: a crystallographic and ab initio inquiry into the nature of silicon-oxygen interactions

Soroosh Shambayati, Stuart L. Schreiber, James F. Blake et al. · Journal of the American Chemical Society · 1990 · 187 citations

, , +11

The directed reduction of β-hydroxy ketones employing Me4NHB(OAc)3

David A. Evans, Kevin T. Chapman · Tetrahedron Letters · 1986 · 185 citations

, , +6