Rhodium-catalyzed conjugate addition-enantioselective protonation: The synthesis of α,α′-dibenzyl esters

Christopher G. Frost; Stephen D. Penrose; Kim Lambshead; Paul R. Raithby; John E. Warren; Robert Gleave

doi:10.1021/ol070603g

Rhodium-catalyzed conjugate addition-enantioselective protonation: The synthesis of α,α′-dibenzyl esters

Christopher G. Frost, Stephen D. Penrose, Kim Lambshead, Paul R. Raithby, John E. Warren, Robert Gleave

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

Abstract

α-Benzyl acrylates, which are conveniently prepared from the corresponding aldehydes, can be employed as substrates in a tandem rhodiumcatalyzed conjugate addition-enantioselective protonation protocol to afford enantiomerically enriched α,α′-dibenzyl esters. The synergistic effect of enantiopure ligand and proton source was rapidly optimized with use of a microwave reactor. © 2007 American Chemical Society.

Original language	English
Pages (from-to)	2119-2122
Number of pages	3
Journal	Organic Letters
Volume	9
Issue number	11
DOIs	https://doi.org/10.1021/ol070603g
Publication status	Published - 24 May 2007

Keywords

4-ADDITION
ORGANOBORONIC ACIDS
ARYLBORONIC ACIDS
PART 2
{DERIVATIVES
CYCLIZATION
CHEMISTRY
LIGANDS
BORON
ACIDS
{ACIDS
ARYLBORONIC} {ACIDS
{ASYMMETRIC} 1
DERIVATIVES
ELECTRON-DEFICIENT} {OLEFINS
{ELECTRON-DEFICIENT} {OLEFINS
ASYMMETRIC 1
ORGANOBORONIC
{LIGANDS
{PART} 2

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10.1021/ol070603g

CCDC 639247: Experimental Crystal Structure Determination
Frost, C. G. (Contributor), Penrose, S. D. (Contributor), Lambshead, K. (Contributor), Raithby, P. R. (Contributor), Warren, J. (Contributor) & Gleave, R. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2007
DOI: 10.5517/ccpg5w5, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccpg5w5&sid=DataCite
Dataset

Cite this

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title = "Rhodium-catalyzed conjugate addition-enantioselective protonation: The synthesis of α,α′-dibenzyl esters",

abstract = "α-Benzyl acrylates, which are conveniently prepared from the corresponding aldehydes, can be employed as substrates in a tandem rhodiumcatalyzed conjugate addition-enantioselective protonation protocol to afford enantiomerically enriched α,α′-dibenzyl esters. The synergistic effect of enantiopure ligand and proton source was rapidly optimized with use of a microwave reactor. {\textcopyright} 2007 American Chemical Society.",

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author = "Frost, {Christopher G.} and Penrose, {Stephen D.} and Kim Lambshead and Raithby, {Paul R.} and Warren, {John E.} and Robert Gleave",

note = "11",

year = "2007",

month = may,

day = "24",

doi = "10.1021/ol070603g",

language = "English",

volume = "9",

pages = "2119--2122",

journal = "Organic Letters",

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publisher = "American Chemical Society",

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TY - JOUR

T1 - Rhodium-catalyzed conjugate addition-enantioselective protonation: The synthesis of α,α′-dibenzyl esters

AU - Frost, Christopher G.

AU - Penrose, Stephen D.

AU - Lambshead, Kim

AU - Raithby, Paul R.

AU - Warren, John E.

AU - Gleave, Robert

N1 - 11

PY - 2007/5/24

Y1 - 2007/5/24

N2 - α-Benzyl acrylates, which are conveniently prepared from the corresponding aldehydes, can be employed as substrates in a tandem rhodiumcatalyzed conjugate addition-enantioselective protonation protocol to afford enantiomerically enriched α,α′-dibenzyl esters. The synergistic effect of enantiopure ligand and proton source was rapidly optimized with use of a microwave reactor. © 2007 American Chemical Society.

AB - α-Benzyl acrylates, which are conveniently prepared from the corresponding aldehydes, can be employed as substrates in a tandem rhodiumcatalyzed conjugate addition-enantioselective protonation protocol to afford enantiomerically enriched α,α′-dibenzyl esters. The synergistic effect of enantiopure ligand and proton source was rapidly optimized with use of a microwave reactor. © 2007 American Chemical Society.

KW - 4-ADDITION

KW - ORGANOBORONIC ACIDS

KW - ARYLBORONIC ACIDS

KW - PART 2

KW - {DERIVATIVES

KW - CYCLIZATION

KW - CHEMISTRY

KW - LIGANDS

KW - BORON

KW - ACIDS

KW - {ACIDS

KW - ARYLBORONIC} {ACIDS

KW - {ASYMMETRIC} 1

KW - DERIVATIVES

KW - ELECTRON-DEFICIENT} {OLEFINS

KW - {ELECTRON-DEFICIENT} {OLEFINS

KW - ASYMMETRIC 1

KW - ORGANOBORONIC

KW - {LIGANDS

KW - {PART} 2

U2 - 10.1021/ol070603g

DO - 10.1021/ol070603g

M3 - Article

SN - 1523-7052

VL - 9

SP - 2119

EP - 2122

JO - Organic Letters

JF - Organic Letters

IS - 11

ER -

Rhodium-catalyzed conjugate addition-enantioselective protonation: The synthesis of α,α′-dibenzyl esters

Abstract

Keywords

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Datasets

CCDC 639247: Experimental Crystal Structure Determination

Cite this