Enantioselective alkylation of acyclic α,α-disubstituted tributyltin enolates catalyzed by a {Cr(salen)} complex

Abigail G. Doyle; Eric N. Jacobsen

doi:10.1002/anie.200604901

Enantioselective alkylation of acyclic α,α-disubstituted tributyltin enolates catalyzed by a {Cr(salen)} complex

Abigail G. Doyle
, Eric N. Jacobsen

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

95 Scopus citations

Abstract

Straighten out the mixture: A dynamic mixture of acyclic isomers of tributyltin enolates undergoes a {Cr(salen)}-catalyzed alkylation reaction to generate methyl ketones that contain α-carbonyl quaternary stereocenters in high yield and enantioselectivity (salen = N,N′-bis(salicylidene) ethylenediamine dianion). A mechanism is proposed which involves halide activation by a cationic metal complex. (Chemical Equation Presented).

Original language	English (US)
Pages (from-to)	3701-3705
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	46
Issue number	20
DOIs	https://doi.org/10.1002/anie.200604901
State	Published - 2007

All Science Journal Classification (ASJC) codes

Catalysis
General Chemistry

Keywords

Alkylation
Asymmetric catalysis
Chromium
Enolates
N,O ligands

Access to Document

10.1002/anie.200604901

Cite this

@article{5c4c4780df3d4791b8f0f07321e1677e,

title = "Enantioselective alkylation of acyclic α,α-disubstituted tributyltin enolates catalyzed by a \{Cr(salen)\} complex",

abstract = "Straighten out the mixture: A dynamic mixture of acyclic isomers of tributyltin enolates undergoes a \{Cr(salen)\}-catalyzed alkylation reaction to generate methyl ketones that contain α-carbonyl quaternary stereocenters in high yield and enantioselectivity (salen = N,N′-bis(salicylidene) ethylenediamine dianion). A mechanism is proposed which involves halide activation by a cationic metal complex. (Chemical Equation Presented).",

keywords = "Alkylation, Asymmetric catalysis, Chromium, Enolates, N,O ligands",

author = "Doyle, \{Abigail G.\} and Jacobsen, \{Eric N.\}",

year = "2007",

doi = "10.1002/anie.200604901",

language = "English (US)",

volume = "46",

pages = "3701--3705",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

publisher = "John Wiley and Sons Ltd",

number = "20",

}

TY - JOUR

T1 - Enantioselective alkylation of acyclic α,α-disubstituted tributyltin enolates catalyzed by a {Cr(salen)} complex

AU - Doyle, Abigail G.

AU - Jacobsen, Eric N.

PY - 2007

Y1 - 2007

N2 - Straighten out the mixture: A dynamic mixture of acyclic isomers of tributyltin enolates undergoes a {Cr(salen)}-catalyzed alkylation reaction to generate methyl ketones that contain α-carbonyl quaternary stereocenters in high yield and enantioselectivity (salen = N,N′-bis(salicylidene) ethylenediamine dianion). A mechanism is proposed which involves halide activation by a cationic metal complex. (Chemical Equation Presented).

AB - Straighten out the mixture: A dynamic mixture of acyclic isomers of tributyltin enolates undergoes a {Cr(salen)}-catalyzed alkylation reaction to generate methyl ketones that contain α-carbonyl quaternary stereocenters in high yield and enantioselectivity (salen = N,N′-bis(salicylidene) ethylenediamine dianion). A mechanism is proposed which involves halide activation by a cationic metal complex. (Chemical Equation Presented).

KW - Alkylation

KW - Asymmetric catalysis

KW - Chromium

KW - Enolates

KW - N,O ligands

UR - https://www.scopus.com/pages/publications/34250891887

UR - https://www.scopus.com/pages/publications/34250891887#tab=citedBy

U2 - 10.1002/anie.200604901

DO - 10.1002/anie.200604901

M3 - Article

C2 - 17407117

AN - SCOPUS:34250891887

SN - 1433-7851

VL - 46

SP - 3701

EP - 3705

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 20

ER -

Enantioselective alkylation of acyclic α,α-disubstituted tributyltin enolates catalyzed by a {Cr(salen)} complex

Abstract

All Science Journal Classification (ASJC) codes

Keywords

Access to Document

Other files and links

Fingerprint

Cite this