Enantioconvergent Fukuyama Cross-Coupling of Racemic Benzylic Organozinc Reagents

Rik Oost; Antonio Misale; Nuno Maulide

doi:10.1002/anie.201600597

Enantioconvergent Fukuyama Cross-Coupling of Racemic Benzylic Organozinc Reagents

Rik Oost, Antonio Misale, Nuno Maulide (Corresponding author)

Department of Organic Chemistry

Publications: Contribution to journal › Short communication › Peer Reviewed

Abstract

The first enantioconvergent palladium-catalyzed Fukuyama cross-coupling of racemic benzylic organozinc reagents with thioesters has been developed. The reaction furnishes enantioenriched acyclic α-disubstituted ketone products in good yields and high enantioselectivities. A broad substrate scope is achieved under mild reaction conditions to prevent racemization of the potentially labile tertiary stereocenters.

Original language	English
Pages (from-to)	4587-4590
Number of pages	4
Journal	Angewandte Chemie (International Edition)
Volume	55
Issue number	14
DOIs	https://doi.org/10.1002/anie.201600597
Publication status	Published - 24 Mar 2016

Austrian Fields of Science 2012

104015 Organic chemistry

Keywords

cross-coupling
enantioselectivity
ligand effects
palladium
zinc
MAGNETIC-RESONANCE-SPECTROSCOPY
CONFIGURATIONAL STABILITY
STEREOSELECTIVE PREPARATION
ALPHA-BROMOKETONES
ACYCLIC KETONES
LIGANDS
HALIDES
ALKYLATIONS
CATALYST
BOND

Access to Document

10.1002/anie.201600597

Cite this

@article{104dd440bc984a83842d02e48852b3a3,

title = "Enantioconvergent Fukuyama Cross-Coupling of Racemic Benzylic Organozinc Reagents",

abstract = "The first enantioconvergent palladium-catalyzed Fukuyama cross-coupling of racemic benzylic organozinc reagents with thioesters has been developed. The reaction furnishes enantioenriched acyclic α-disubstituted ketone products in good yields and high enantioselectivities. A broad substrate scope is achieved under mild reaction conditions to prevent racemization of the potentially labile tertiary stereocenters.",

keywords = "cross-coupling, enantioselectivity, ligand effects, palladium, zinc, MAGNETIC-RESONANCE-SPECTROSCOPY, CONFIGURATIONAL STABILITY, STEREOSELECTIVE PREPARATION, ALPHA-BROMOKETONES, ACYCLIC KETONES, LIGANDS, HALIDES, ALKYLATIONS, CATALYST, BOND",

author = "Rik Oost and Antonio Misale and Nuno Maulide",

note = "Publisher Copyright: {\textcopyright} 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.",

year = "2016",

month = mar,

day = "24",

doi = "10.1002/anie.201600597",

language = "English",

volume = "55",

pages = "4587--4590",

journal = "Angewandte Chemie (International Edition)",

issn = "1433-7851",

publisher = "WILEY-V C H VERLAG GMBH",

number = "14",

}

TY - JOUR

T1 - Enantioconvergent Fukuyama Cross-Coupling of Racemic Benzylic Organozinc Reagents

AU - Oost, Rik

AU - Misale, Antonio

AU - Maulide, Nuno

PY - 2016/3/24

Y1 - 2016/3/24

N2 - The first enantioconvergent palladium-catalyzed Fukuyama cross-coupling of racemic benzylic organozinc reagents with thioesters has been developed. The reaction furnishes enantioenriched acyclic α-disubstituted ketone products in good yields and high enantioselectivities. A broad substrate scope is achieved under mild reaction conditions to prevent racemization of the potentially labile tertiary stereocenters.

AB - The first enantioconvergent palladium-catalyzed Fukuyama cross-coupling of racemic benzylic organozinc reagents with thioesters has been developed. The reaction furnishes enantioenriched acyclic α-disubstituted ketone products in good yields and high enantioselectivities. A broad substrate scope is achieved under mild reaction conditions to prevent racemization of the potentially labile tertiary stereocenters.

KW - cross-coupling

KW - enantioselectivity

KW - ligand effects

KW - palladium

KW - zinc

KW - MAGNETIC-RESONANCE-SPECTROSCOPY

KW - CONFIGURATIONAL STABILITY

KW - STEREOSELECTIVE PREPARATION

KW - ALPHA-BROMOKETONES

KW - ACYCLIC KETONES

KW - LIGANDS

KW - HALIDES

KW - ALKYLATIONS

KW - CATALYST

KW - BOND

UR - http://www.scopus.com/inward/record.url?scp=84959458490&partnerID=8YFLogxK

U2 - 10.1002/anie.201600597

DO - 10.1002/anie.201600597

M3 - Short communication

VL - 55

SP - 4587

EP - 4590

JO - Angewandte Chemie (International Edition)

JF - Angewandte Chemie (International Edition)

SN - 1433-7851

IS - 14

ER -

Enantioconvergent Fukuyama Cross-Coupling of Racemic Benzylic Organozinc Reagents

Abstract

Austrian Fields of Science 2012

Keywords

Access to Document

Other files and links

Cite this