Copper phosphoramidite-catalyzed enantioselective desymmetrization of meso-cyclic allylic bisdiethyl phosphates

Umberto Piarulli; Christelle Claverie; Philippe Daubos; Cesare Gennari; Adriaan J. Minnaard; Bernard Feringa

doi:10.1021/ol035801l

Copper phosphoramidite-catalyzed enantioselective desymmetrization of meso-cyclic allylic bisdiethyl phosphates

Umberto Piarulli
, Christelle Claverie
, Philippe Daubos
, Cesare Gennari
, Adriaan J. Minnaard
, Bernard Feringa

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

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Abstract

A highly regio-, diastereo-, and enantioselective desymmetrization of five-, six-, and seven-membered meso-cyclic allylic bis-diethyl phosphates (2a, 2b, and 2c, respectively) was obtained with diethylzinc, using catalytic amounts of [Cu(OTf)](2).C6H6 and phosphoramidite ligands 5. Enantiomeric excesses of up to 87, 94, and >98% were obtained for the addition of diethylzinc to cyclopentene, cyclohexene, and cycloheptene bis-diethyl phosphates, respectively.

Original language	English
Pages (from-to)	4493-4496
Number of pages	4
Journal	Organic letters
Volume	5
Issue number	23
DOIs	https://doi.org/10.1021/ol035801l
Publication status	Published - 13-Nov-2003

Keywords

OXABICYCLIC ALKENES
CHEMICAL-SHIFTS
LIGANDS

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@article{0f98763a066a48eeba41e96470ca994e,

title = "Copper phosphoramidite-catalyzed enantioselective desymmetrization of meso-cyclic allylic bisdiethyl phosphates",

abstract = "A highly regio-, diastereo-, and enantioselective desymmetrization of five-, six-, and seven-membered meso-cyclic allylic bis-diethyl phosphates (2a, 2b, and 2c, respectively) was obtained with diethylzinc, using catalytic amounts of [Cu(OTf)](2).C6H6 and phosphoramidite ligands 5. Enantiomeric excesses of up to 87, 94, and >98\% were obtained for the addition of diethylzinc to cyclopentene, cyclohexene, and cycloheptene bis-diethyl phosphates, respectively.",

keywords = "OXABICYCLIC ALKENES, CHEMICAL-SHIFTS, LIGANDS",

author = "Umberto Piarulli and Christelle Claverie and Philippe Daubos and Cesare Gennari and Minnaard, \{Adriaan J.\} and Bernard Feringa",

note = "Relation: http://www.rug.nl/scheikunde/ date\_submitted:2005 Rights: University of Groningen. Stratingh Institute",

year = "2003",

month = nov,

day = "13",

doi = "10.1021/ol035801l",

language = "English",

volume = "5",

pages = "4493--4496",

journal = "Organic letters",

issn = "1523-7060",

publisher = "AMER CHEMICAL SOC INC",

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}

TY - JOUR

T1 - Copper phosphoramidite-catalyzed enantioselective desymmetrization of meso-cyclic allylic bisdiethyl phosphates

AU - Piarulli, Umberto

AU - Claverie, Christelle

AU - Daubos, Philippe

AU - Gennari, Cesare

AU - Minnaard, Adriaan J.

AU - Feringa, Bernard

N1 - Relation: http://www.rug.nl/scheikunde/ date_submitted:2005 Rights: University of Groningen. Stratingh Institute

PY - 2003/11/13

Y1 - 2003/11/13

N2 - A highly regio-, diastereo-, and enantioselective desymmetrization of five-, six-, and seven-membered meso-cyclic allylic bis-diethyl phosphates (2a, 2b, and 2c, respectively) was obtained with diethylzinc, using catalytic amounts of [Cu(OTf)](2).C6H6 and phosphoramidite ligands 5. Enantiomeric excesses of up to 87, 94, and >98% were obtained for the addition of diethylzinc to cyclopentene, cyclohexene, and cycloheptene bis-diethyl phosphates, respectively.

AB - A highly regio-, diastereo-, and enantioselective desymmetrization of five-, six-, and seven-membered meso-cyclic allylic bis-diethyl phosphates (2a, 2b, and 2c, respectively) was obtained with diethylzinc, using catalytic amounts of [Cu(OTf)](2).C6H6 and phosphoramidite ligands 5. Enantiomeric excesses of up to 87, 94, and >98% were obtained for the addition of diethylzinc to cyclopentene, cyclohexene, and cycloheptene bis-diethyl phosphates, respectively.

KW - OXABICYCLIC ALKENES

KW - CHEMICAL-SHIFTS

KW - LIGANDS

U2 - 10.1021/ol035801l

DO - 10.1021/ol035801l

M3 - Article

SN - 1523-7060

VL - 5

SP - 4493

EP - 4496

JO - Organic letters

JF - Organic letters

IS - 23

ER -

Copper phosphoramidite-catalyzed enantioselective desymmetrization of meso-cyclic allylic bisdiethyl phosphates

Abstract

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