Diastereoselective self-assembly of chiral diamine-chelated aryllithiums to dimeric aggregates

Anne M. Arink; Claudia M. P. Kronenburg; Johann T. B. H. Jastrzebski; Martin Lutz; Anthony L. Spek; Robert A. Gossage; Gerard Van Koten

doi:10.1021/ja045914q

Diastereoselective self-assembly of chiral diamine-chelated aryllithiums to dimeric aggregates

Anne M. Arink, Claudia M. P. Kronenburg, Johann T. B. H. Jastrzebski, Martin Lutz, Anthony L. Spek, Robert A. Gossage, Gerard Van Koten

Sub Organic Chemistry and Catalysis

Research output: Contribution to journal › Article › Academic › peer-review

Abstract

Aryllithium compounds [LiC6H4(CH2N(Et) CH2CH2NEt2)-2]2(2b), [LiC6H4(CH(Me)N(Me)CH2-CH2NMe2-(R))-2]2((R)-3b), and [LiC6H4(CH(Me)N(Me)CH2CH2NMe2-(rac))-2]2((rac)-3b) were synthesized and characterized in the solid state and in solution. X-ray crystallographic studies of 2b and (R)-3b and molecular weight determinations of 2b, (R)-3b, and (rac)-3b by cryoscopy in benzene showed that, both in the solid state and in apolar, noncoordinating solvents such as benzene, these compounds exist as discrete dimeric aggregates. For (R)-3b and (rac)-3b the aggregation process of two monomeric aryllithium units to one dimer is highly diastereoselective.

Original language	English
Pages (from-to)	16249-16258
Number of pages	10
Journal	Journal of the American Chemical Society
Volume	126
Issue number	49
DOIs	https://doi.org/10.1021/ja045914q
Publication status	Published - 15 Dec 2004

Keywords

diamine
dimer
lithium derivative
article
chemical reaction
chirality
combinatorial chemistry
diastereoisomer
dimerization
molecular interaction
molecular weight
reaction analysis
solid state
X ray crystallography

Access to Document

10.1021/ja045914q

10
Open Access (free)

Cite this

@article{ad34c7fd6407457bb99a341bfe370c37,

title = "Diastereoselective self-assembly of chiral diamine-chelated aryllithiums to dimeric aggregates",

abstract = "Aryllithium compounds [LiC6H4(CH2N(Et) CH2CH2NEt2)-2]2(2b), [LiC6H4(CH(Me)N(Me)CH2-CH2NMe2-(R))-2]2((R)-3b), and [LiC6H4(CH(Me)N(Me)CH2CH2NMe2-(rac))-2]2((rac)-3b) were synthesized and characterized in the solid state and in solution. X-ray crystallographic studies of 2b and (R)-3b and molecular weight determinations of 2b, (R)-3b, and (rac)-3b by cryoscopy in benzene showed that, both in the solid state and in apolar, noncoordinating solvents such as benzene, these compounds exist as discrete dimeric aggregates. For (R)-3b and (rac)-3b the aggregation process of two monomeric aryllithium units to one dimer is highly diastereoselective.",

keywords = "diamine, dimer, lithium derivative, article, chemical reaction, chirality, combinatorial chemistry, diastereoisomer, dimerization, molecular interaction, molecular weight, reaction analysis, solid state, X ray crystallography",

author = "Arink, {Anne M.} and Kronenburg, {Claudia M. P.} and Jastrzebski, {Johann T. B. H.} and Martin Lutz and Spek, {Anthony L.} and Gossage, {Robert A.} and {Van Koten}, Gerard",

year = "2004",

month = dec,

day = "15",

doi = "10.1021/ja045914q",

language = "English",

volume = "126",

pages = "16249--16258",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society",

number = "49",

}

TY - JOUR

T1 - Diastereoselective self-assembly of chiral diamine-chelated aryllithiums to dimeric aggregates

AU - Arink, Anne M.

AU - Kronenburg, Claudia M. P.

AU - Jastrzebski, Johann T. B. H.

AU - Lutz, Martin

AU - Spek, Anthony L.

AU - Gossage, Robert A.

AU - Van Koten, Gerard

PY - 2004/12/15

Y1 - 2004/12/15

N2 - Aryllithium compounds [LiC6H4(CH2N(Et) CH2CH2NEt2)-2]2(2b), [LiC6H4(CH(Me)N(Me)CH2-CH2NMe2-(R))-2]2((R)-3b), and [LiC6H4(CH(Me)N(Me)CH2CH2NMe2-(rac))-2]2((rac)-3b) were synthesized and characterized in the solid state and in solution. X-ray crystallographic studies of 2b and (R)-3b and molecular weight determinations of 2b, (R)-3b, and (rac)-3b by cryoscopy in benzene showed that, both in the solid state and in apolar, noncoordinating solvents such as benzene, these compounds exist as discrete dimeric aggregates. For (R)-3b and (rac)-3b the aggregation process of two monomeric aryllithium units to one dimer is highly diastereoselective.

AB - Aryllithium compounds [LiC6H4(CH2N(Et) CH2CH2NEt2)-2]2(2b), [LiC6H4(CH(Me)N(Me)CH2-CH2NMe2-(R))-2]2((R)-3b), and [LiC6H4(CH(Me)N(Me)CH2CH2NMe2-(rac))-2]2((rac)-3b) were synthesized and characterized in the solid state and in solution. X-ray crystallographic studies of 2b and (R)-3b and molecular weight determinations of 2b, (R)-3b, and (rac)-3b by cryoscopy in benzene showed that, both in the solid state and in apolar, noncoordinating solvents such as benzene, these compounds exist as discrete dimeric aggregates. For (R)-3b and (rac)-3b the aggregation process of two monomeric aryllithium units to one dimer is highly diastereoselective.

KW - diamine

KW - dimer

KW - lithium derivative

KW - article

KW - chemical reaction

KW - chirality

KW - combinatorial chemistry

KW - diastereoisomer

KW - dimerization

KW - molecular interaction

KW - molecular weight

KW - reaction analysis

KW - solid state

KW - X ray crystallography

U2 - 10.1021/ja045914q

DO - 10.1021/ja045914q

M3 - Article

SN - 0002-7863

VL - 126

SP - 16249

EP - 16258

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 49

ER -

Diastereoselective self-assembly of chiral diamine-chelated aryllithiums to dimeric aggregates

Abstract

Keywords

Access to Document

Fingerprint

Cite this