Enantioselective addition of organometallics to aldehydes using camphor derived chiral 1,4-aminoalcohols as ligands

Knollmüller, Max; Ferencic, Mathias; Gärtner, Peter

doi:10.1016/s0957-4166(99)00413-9

Cited by 43 publications

(9 citation statements)

References 22 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Knollmüller et al employed seven camphor-derived aminoalcohols and achieved with 12 up to 32% ee of (R)-1phenyl-1-pentanol (5.2:9.2:1 ratio, in Et 2 O at -78°C). 32 For all ligands, diethyl ether was found to give enantioselectivities superior to those obtained with THF.…”

Section: Biographical Sketchmentioning

confidence: 92%

Organolithiums in Enantioselective Additions to π* and σ* Carbon-Oxygen Electrophiles

Goldfuß¹

2005

Synthesis

View full text Add to dashboard Cite

Mediated by chiral, non-racemic ligands, organolithiums add enantioselectively to C=O functions of carbonyl compounds (aldehydes and ketones) or cleave enantioselectively C-O units in strained ethers (epoxides and oxetanes) as well as in acetals. The achievement of high enantioselectivities is desirable and hence factors controlling these enantioselectivities are the subject of intensive research. Beneficial external influences on enantioselectivity are low temperatures, suitable solvents (e.g. dimethoxymethane, dimethyl ether) and the exclusion of salt impurities. Organolithium reagents and ligands lithiated in situ form mixed anionic aggregates, some of which can be isolated and even structurally studied. The improved understanding of the nature of such chiral organolithium aggregates provides the way to a more rational design of new enantioselective organolithium reagents.

show abstract

Section: Biographical Sketchmentioning

confidence: 92%

Organolithiums in Enantioselective Additions to π* and σ* Carbon-Oxygen Electrophiles

Goldfuß¹

2005

Synthesis

View full text Add to dashboard Cite

show abstract

“…Articles describing the preparation and use of novel ligands for this transformation are cited here. [103][104][105][106][107][108][109][110][111][112][113][114][115][116][117][118][119][120] Papers which introduce significant modifications to existing methodology will be discussed in more detail. The titanium-catalysed addition of diethylzinc to aldehydes has received somewhat less attention.…”

Section: Carbon-carbon Bond Forming Reactions 231 Addition Of Carbon ...mentioning

confidence: 99%

Catalytic asymmetric processes

Tye

Comina

2001

J. Chem. Soc., Perkin Trans. 1

View full text Add to dashboard Cite

“…1). [4][5][6][7] In these cases the ligand structure is formed by a rigid camphor or camphor-like core bearing the hydroxyl group. The amino group is normally bound to the core through an aliphatic chain (Fig.…”

Section: Introductionmentioning

confidence: 99%

Enantioselective addition of diethylzinc to aldehydes using 1,4-aminoalcohols as chiral ligands

Scarpi

Galbo

Occhiato

et al. 2004

Tetrahedron: Asymmetry

View full text Add to dashboard Cite

Enantioselective addition of organometallics to aldehydes using camphor derived chiral 1,4-aminoalcohols as ligands

Cited by 43 publications

References 22 publications

Organolithiums in Enantioselective Additions to π* and σ* Carbon-Oxygen Electrophiles

Organolithiums in Enantioselective Additions to π* and σ* Carbon-Oxygen Electrophiles

Catalytic asymmetric processes

Enantioselective addition of diethylzinc to aldehydes using 1,4-aminoalcohols as chiral ligands

Contact Info

Product

Resources

About