Rhodium-catalyzed conjugate addition-enantioselective protonation: The synthesis of alpha,alpha'-dibenzyl esters

C G Frost; S D Penrose; K Lambshead; P R Raithby; J E Warren; R GleaveO

doi:10.1021/ol070603g

Rhodium-catalyzed conjugate addition-enantioselective protonation: The synthesis of alpha,alpha'-dibenzyl esters

C G Frost, S D Penrose, K Lambshead, P R Raithby, J E Warren, R GleaveO

Department of Chemistry

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

51 Citations (SciVal)

Abstract

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

Original language	English
Pages (from-to)	2119-2122
Number of pages	4
Journal	Organic Letters
Volume	9
Issue number	11
DOIs	https://doi.org/10.1021/ol070603g
Publication status	Published - 2007

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

abstract = "alpha-Benzyl acrylates, which are conveniently prepared from the corresponding aldehydes, can be employed as substrates in a tandem rhodium-catalyzed conjugate addition-enantioselective protonation protocol to afford enantiomerically enriched alpha, alpha'-dibenzyl esters. The synergistic effect of enantiopure ligand and proton source was rapidly optimized with use of a microwave reactor.",

author = "Frost, {C G} and Penrose, {S D} and K Lambshead and Raithby, {P R} and Warren, {J E} and R GleaveO",

year = "2007",

doi = "10.1021/ol070603g",

language = "English",

volume = "9",

pages = "2119--2122",

journal = "Organic Letters",

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T1 - Rhodium-catalyzed conjugate addition-enantioselective protonation: The synthesis of alpha,alpha'-dibenzyl esters

AU - Frost, C G

AU - Penrose, S D

AU - Lambshead, K

AU - Raithby, P R

AU - Warren, J E

AU - GleaveO, R

PY - 2007

Y1 - 2007

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

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

UR - http://dx.doi.org/10.1021/ol070603g

U2 - 10.1021/ol070603g

DO - 10.1021/ol070603g

M3 - Article

SN - 1523-7060

VL - 9

SP - 2119

EP - 2122

JO - Organic Letters

JF - Organic Letters

IS - 11

ER -

Rhodium-catalyzed conjugate addition-enantioselective protonation: The synthesis of alpha,alpha'-dibenzyl esters

Abstract

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