Highly enantio- and diastereoselective one-pot reactions in aqueous media: Combined asymmetric Rh-catalyzed conjugate addition/metal-mediated allylation

Sara Kallstrom; Richard B. C. Jagt; Reijo Sillanpaa; Ben L. Feringa; Adriaan J. Minnaard; Reko Leino; Sara Källström; Reijo Sillanpää

doi:10.1002/ejoc.200600309

Highly enantio- and diastereoselective one-pot reactions in aqueous media: Combined asymmetric Rh-catalyzed conjugate addition/metal-mediated allylation

Sara Kallstrom^*, Richard B. C. Jagt, Reijo Sillanpaa, Ben L. Feringa, Adriaan J. Minnaard, Reko Leino, Sara Källström, Reijo Sillanpää

^*Bijbehorende auteur voor dit werk

Onderzoeksoutput › Academic › peer review

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1,3-Disubstituted, enantiopure cyclohexanols have been prepared in very high diastereoselectivities and good yields by a concise one-pot method combining the enantioselective rhodium-catalyzed conjugate addition of arylboronic acids with indium-mediated allylation into a highly efficient one-pot reaction in aqueous media. (c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006.

Originele taal-2	English
Pagina's (van-tot)	3826-3833
Aantal pagina's	8
Tijdschrift	European Journal of Organic Chemistry
Nummer van het tijdschrift	17
DOI's	https://doi.org/10.1002/ejoc.200600309
Status	Published - 25-aug-2006

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CCDC 298839: Experimental Crystal Structure Determination
Källström, S. (Contributor), Jagt, R. B. C. (Contributor), Sillanpää, R. (Contributor), Feringa, B. L. (Contributor), Minnaard, A. (Contributor) & Leino, R. (Contributor), University of Groningen, 17-feb-2006
DOI: 10.5517/ccb0yz7
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Kallstrom, S., Jagt, R. B. C., Sillanpaa, R., Feringa, B. L., Minnaard, A. J., Leino, R., Källström, S., & Sillanpää, R. (2006). Highly enantio- and diastereoselective one-pot reactions in aqueous media: Combined asymmetric Rh-catalyzed conjugate addition/metal-mediated allylation. European Journal of Organic Chemistry, (17), 3826-3833. https://doi.org/10.1002/ejoc.200600309

Kallstrom, Sara ; Jagt, Richard B. C. ; Sillanpaa, Reijo ; Feringa, Ben L. ; Minnaard, Adriaan J. ; Leino, Reko ; Källström, Sara ; Sillanpää, Reijo. / Highly enantio- and diastereoselective one-pot reactions in aqueous media : Combined asymmetric Rh-catalyzed conjugate addition/metal-mediated allylation. In: European Journal of Organic Chemistry. 2006 ; Nr. 17. blz. 3826-3833.

@article{62713c88ac0f4aa08c3508de011bc8d7,

title = "Highly enantio- and diastereoselective one-pot reactions in aqueous media: Combined asymmetric Rh-catalyzed conjugate addition/metal-mediated allylation",

abstract = "1,3-Disubstituted, enantiopure cyclohexanols have been prepared in very high diastereoselectivities and good yields by a concise one-pot method combining the enantioselective rhodium-catalyzed conjugate addition of arylboronic acids with indium-mediated allylation into a highly efficient one-pot reaction in aqueous media. (c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006.",

keywords = "asymmetric synthesis, conjugate addition, allylation, diastereoselectivity, ELECTRON-DEFICIENT OLEFINS, RING-CLOSING METATHESIS, BOND-FORMING REACTIONS, ARYLBORONIC ACIDS, MONODENTATE PHOSPHORAMIDITES, ORGANOMETALLIC COMPOUNDS, ALKENYLBORONIC ACIDS, ORGANOBORONIC ACIDS, ORGANIC-SYNTHESIS, BORONIC ACIDS",

author = "Sara Kallstrom and Jagt, {Richard B. C.} and Reijo Sillanpaa and Feringa, {Ben L.} and Minnaard, {Adriaan J.} and Reko Leino and Sara K{\"a}llstr{\"o}m and Reijo Sillanp{\"a}{\"a}",

year = "2006",

month = aug,

day = "25",

doi = "10.1002/ejoc.200600309",

language = "English",

pages = "3826--3833",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

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

number = "17",

}

Kallstrom, S, Jagt, RBC, Sillanpaa, R, Feringa, BL , Minnaard, AJ, Leino, R, Källström, S & Sillanpää, R 2006, 'Highly enantio- and diastereoselective one-pot reactions in aqueous media: Combined asymmetric Rh-catalyzed conjugate addition/metal-mediated allylation', European Journal of Organic Chemistry, nr. 17, blz. 3826-3833. https://doi.org/10.1002/ejoc.200600309

Highly enantio- and diastereoselective one-pot reactions in aqueous media : Combined asymmetric Rh-catalyzed conjugate addition/metal-mediated allylation. / Kallstrom, Sara; Jagt, Richard B. C.; Sillanpaa, Reijo; Feringa, Ben L.; Minnaard, Adriaan J.; Leino, Reko; Källström, Sara; Sillanpää, Reijo.

In: European Journal of Organic Chemistry, Nr. 17, 25.08.2006, blz. 3826-3833.

Onderzoeksoutput › Academic › peer review

TY - JOUR

T1 - Highly enantio- and diastereoselective one-pot reactions in aqueous media

T2 - Combined asymmetric Rh-catalyzed conjugate addition/metal-mediated allylation

AU - Kallstrom, Sara

AU - Jagt, Richard B. C.

AU - Sillanpaa, Reijo

AU - Feringa, Ben L.

AU - Minnaard, Adriaan J.

AU - Leino, Reko

AU - Källström, Sara

AU - Sillanpää, Reijo

PY - 2006/8/25

Y1 - 2006/8/25

N2 - 1,3-Disubstituted, enantiopure cyclohexanols have been prepared in very high diastereoselectivities and good yields by a concise one-pot method combining the enantioselective rhodium-catalyzed conjugate addition of arylboronic acids with indium-mediated allylation into a highly efficient one-pot reaction in aqueous media. (c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006.

AB - 1,3-Disubstituted, enantiopure cyclohexanols have been prepared in very high diastereoselectivities and good yields by a concise one-pot method combining the enantioselective rhodium-catalyzed conjugate addition of arylboronic acids with indium-mediated allylation into a highly efficient one-pot reaction in aqueous media. (c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006.

KW - asymmetric synthesis

KW - conjugate addition

KW - allylation

KW - diastereoselectivity

KW - ELECTRON-DEFICIENT OLEFINS

KW - RING-CLOSING METATHESIS

KW - BOND-FORMING REACTIONS

KW - ARYLBORONIC ACIDS

KW - MONODENTATE PHOSPHORAMIDITES

KW - ORGANOMETALLIC COMPOUNDS

KW - ALKENYLBORONIC ACIDS

KW - ORGANOBORONIC ACIDS

KW - ORGANIC-SYNTHESIS

KW - BORONIC ACIDS

U2 - 10.1002/ejoc.200600309

DO - 10.1002/ejoc.200600309

M3 - Article

SP - 3826

EP - 3833

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

SN - 1434-193X

IS - 17

ER -

Highly enantio- and diastereoselective one-pot reactions in aqueous media: Combined asymmetric Rh-catalyzed conjugate addition/metal-mediated allylation

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CCDC 298839: Experimental Crystal Structure Determination

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