Chiral Diarylmethanes via Copper-Catalyzed Asymmetric Allylic Arylation with Organolithium Compounds

Sureshbabu Guduguntla; Valentin Hornillos; Romain Tessier; Martin Fananas-Mastral; Ben L. Feringa

doi:10.1021/acs.orglett.5b03396

Chiral Diarylmethanes via Copper-Catalyzed Asymmetric Allylic Arylation with Organolithium Compounds

Sureshbabu Guduguntla, Valentin Hornillos, Romain Tessier, Martin Fananas-Mastral, Ben L. Feringa

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Abstract

A highly enantioselective copper/N-heterocyclic carbene catalyzed allylic arylation with organolithium compounds is presented. The use of commercial or readily prepared aryllithium reagents in the reaction with allyl bromides affords a variety of chiral diarylvinylmethanes, comprising a privileged structural motif in pharmaceuticals, in high yields with good to excellent regio- and enantioselectivities. The versatility of this new transformation is illustrated in the formal synthesis of the marketed drug tolterodine (Detrol).

Original language	English
Pages (from-to)	252-255
Number of pages	4
Journal	Organic letters
Volume	18
Issue number	2
DOIs	https://doi.org/10.1021/acs.orglett.5b03396
Publication status	Published - 15-Jan-2016

Keywords

PARA-QUINONE METHIDES
GRIGNARD-REAGENTS
STEREOGENIC CENTERS
ENANTIOSELECTIVE SYNTHESIS
SUBSTITUTION-REACTIONS
CONJUGATE ADDITION
ALKYLATION
ARYL
PHOSPHATES
CHLORIDES

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Chiral Diarylmethanes via Copper-Catalyzed AsymmetricFinal publisher's version, 732 KBLicence: Taverne

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title = "Chiral Diarylmethanes via Copper-Catalyzed Asymmetric Allylic Arylation with Organolithium Compounds",

abstract = "A highly enantioselective copper/N-heterocyclic carbene catalyzed allylic arylation with organolithium compounds is presented. The use of commercial or readily prepared aryllithium reagents in the reaction with allyl bromides affords a variety of chiral diarylvinylmethanes, comprising a privileged structural motif in pharmaceuticals, in high yields with good to excellent regio- and enantioselectivities. The versatility of this new transformation is illustrated in the formal synthesis of the marketed drug tolterodine (Detrol).",

keywords = "PARA-QUINONE METHIDES, GRIGNARD-REAGENTS, STEREOGENIC CENTERS, ENANTIOSELECTIVE SYNTHESIS, SUBSTITUTION-REACTIONS, CONJUGATE ADDITION, ALKYLATION, ARYL, PHOSPHATES, CHLORIDES",

author = "Sureshbabu Guduguntla and Valentin Hornillos and Romain Tessier and Martin Fananas-Mastral and Feringa, {Ben L.}",

year = "2016",

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day = "15",

doi = "10.1021/acs.orglett.5b03396",

language = "English",

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T1 - Chiral Diarylmethanes via Copper-Catalyzed Asymmetric Allylic Arylation with Organolithium Compounds

AU - Guduguntla, Sureshbabu

AU - Hornillos, Valentin

AU - Tessier, Romain

AU - Fananas-Mastral, Martin

AU - Feringa, Ben L.

PY - 2016/1/15

Y1 - 2016/1/15

N2 - A highly enantioselective copper/N-heterocyclic carbene catalyzed allylic arylation with organolithium compounds is presented. The use of commercial or readily prepared aryllithium reagents in the reaction with allyl bromides affords a variety of chiral diarylvinylmethanes, comprising a privileged structural motif in pharmaceuticals, in high yields with good to excellent regio- and enantioselectivities. The versatility of this new transformation is illustrated in the formal synthesis of the marketed drug tolterodine (Detrol).

AB - A highly enantioselective copper/N-heterocyclic carbene catalyzed allylic arylation with organolithium compounds is presented. The use of commercial or readily prepared aryllithium reagents in the reaction with allyl bromides affords a variety of chiral diarylvinylmethanes, comprising a privileged structural motif in pharmaceuticals, in high yields with good to excellent regio- and enantioselectivities. The versatility of this new transformation is illustrated in the formal synthesis of the marketed drug tolterodine (Detrol).

KW - PARA-QUINONE METHIDES

KW - GRIGNARD-REAGENTS

KW - STEREOGENIC CENTERS

KW - ENANTIOSELECTIVE SYNTHESIS

KW - SUBSTITUTION-REACTIONS

KW - CONJUGATE ADDITION

KW - ALKYLATION

KW - ARYL

KW - PHOSPHATES

KW - CHLORIDES

U2 - 10.1021/acs.orglett.5b03396

DO - 10.1021/acs.orglett.5b03396

M3 - Article

SN - 1523-7060

VL - 18

SP - 252

EP - 255

JO - Organic letters

JF - Organic letters

IS - 2

ER -

Chiral Diarylmethanes via Copper-Catalyzed Asymmetric Allylic Arylation with Organolithium Compounds

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