Recoverable Dendritic Phase-Transfer Catalysts that Contain (+)-Cinchonine-Derived Ammonium Salts

Jordi Rull; José Juan Jara; Rosa M. Sebastián; Adelina Vallribera; Carmen Nájera; Jean Pierre Majoral; Anne Marie Caminade

doi:10.1002/cctc.201600283

Recoverable Dendritic Phase-Transfer Catalysts that Contain (+)-Cinchonine-Derived Ammonium Salts

Jordi Rull, José Juan Jara, Rosa M. Sebastián, Adelina Vallribera, Carmen Nájera, Jean Pierre Majoral, Anne Marie Caminade

Departament de Química

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KGaA, Weinheim Es preparen quatre nous catalitzadors de transferència de fase dendrimèrics que contenen 12 sals (+)-cinconiniques a la superfície obtingudes per quaternització del N atom de quinuclidina. L'alquilació asimètrica d'una base de Schiff de glicinat amb bromur de bencil s'utilitza com una reacció de referència, i el catalitzador dendrimèric que conté un grup al·lil en el grup O-9 hidroxil de les unitats cinconina és el més actiu. La recuperació i reutilització del catalitzador són possibles per a cinc proves consecutives sense pèrdua d'activitat i amb només una lleugera disminució de l'enantioselectivitat. Si s'utilitzen altres electrofilos, els bromurs de bencil substituïts donen millors resultats que altres bromurs d'alquil activats per donar els corresponents derivats R aminoàcids. Una comparació d'aquests resultats amb els reportats prèviament per a sals similars de cinconina mostra que els dendrimers podrien ser un millor suport que altres polímers per a aquest tipus d'organocatàlisi. © 2016 WILEY-VCH Verlag GmbH

Idioma original	Anglès
Pàgines (de-a)	2049-2056
Revista	ChemCatChem
Volum	8
Número	12
DOIs	https://doi.org/10.1002/cctc.201600283
Estat de la publicació	Publicada - 21 de juny 2016

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@article{0cb3d52031e842af9b54f137fc7dfc6b,

title = "Recoverable Dendritic Phase-Transfer Catalysts that Contain (+)-Cinchonine-Derived Ammonium Salts",

abstract = "{\textcopyright} 2016 WILEY-VCH Verlag GmbH \& Co. KGaA, Weinheim Four new phosphorus dendrimeric phase-transfer catalysts are prepared that contain 12 (+)-cinchoninium salts on the surface obtained by the quaternisation of the quinuclidinic N atom. The asymmetric alkylation of a glycinate Schiff base with benzyl bromide is used as a benchmark reaction, and the dendrimeric catalyst that contains an allyl group on the O-9 hydroxy group of the cinchonine units is the most active. The recovery and reuse of the catalyst are possible for five consecutive runs without loss of activity and with only a slight decrease in enantioselectivity. If other electrophiles are used, substituted benzyl bromides give better results than other activated alkyl bromides to afford the corresponding R amino acid derivatives. A comparison of these results with those reported previously for similar cinchoninium salts shows that dendrimers could be a better support than other polymers for this type of organocatalysis.",

keywords = "alkylation, dendrimers, enantioselectivity, organocatalysis, phase-transfer catalysis",

author = "Jordi Rull and Jara, \{Jos{\'e} Juan\} and Sebasti{\'a}n, \{Rosa M.\} and Adelina Vallribera and Carmen N{\'a}jera and Majoral, \{Jean Pierre\} and Caminade, \{Anne Marie\}",

year = "2016",

month = jun,

day = "21",

doi = "10.1002/cctc.201600283",

language = "English",

volume = "8",

pages = "2049--2056",

journal = "ChemCatChem",

issn = "1867-3880",

publisher = "Wiley - VCH Verlag GmbH \& CO. KGaA",

number = "12",

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TY - JOUR

T1 - Recoverable Dendritic Phase-Transfer Catalysts that Contain (+)-Cinchonine-Derived Ammonium Salts

AU - Rull, Jordi

AU - Jara, José Juan

AU - Sebastián, Rosa M.

AU - Vallribera, Adelina

AU - Nájera, Carmen

AU - Majoral, Jean Pierre

AU - Caminade, Anne Marie

PY - 2016/6/21

Y1 - 2016/6/21

N2 - © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim Four new phosphorus dendrimeric phase-transfer catalysts are prepared that contain 12 (+)-cinchoninium salts on the surface obtained by the quaternisation of the quinuclidinic N atom. The asymmetric alkylation of a glycinate Schiff base with benzyl bromide is used as a benchmark reaction, and the dendrimeric catalyst that contains an allyl group on the O-9 hydroxy group of the cinchonine units is the most active. The recovery and reuse of the catalyst are possible for five consecutive runs without loss of activity and with only a slight decrease in enantioselectivity. If other electrophiles are used, substituted benzyl bromides give better results than other activated alkyl bromides to afford the corresponding R amino acid derivatives. A comparison of these results with those reported previously for similar cinchoninium salts shows that dendrimers could be a better support than other polymers for this type of organocatalysis.

AB - © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim Four new phosphorus dendrimeric phase-transfer catalysts are prepared that contain 12 (+)-cinchoninium salts on the surface obtained by the quaternisation of the quinuclidinic N atom. The asymmetric alkylation of a glycinate Schiff base with benzyl bromide is used as a benchmark reaction, and the dendrimeric catalyst that contains an allyl group on the O-9 hydroxy group of the cinchonine units is the most active. The recovery and reuse of the catalyst are possible for five consecutive runs without loss of activity and with only a slight decrease in enantioselectivity. If other electrophiles are used, substituted benzyl bromides give better results than other activated alkyl bromides to afford the corresponding R amino acid derivatives. A comparison of these results with those reported previously for similar cinchoninium salts shows that dendrimers could be a better support than other polymers for this type of organocatalysis.

KW - alkylation

KW - dendrimers

KW - enantioselectivity

KW - organocatalysis

KW - phase-transfer catalysis

UR - https://www.scopus.com/pages/publications/84973861603

U2 - 10.1002/cctc.201600283

DO - 10.1002/cctc.201600283

M3 - Article

SN - 1867-3880

VL - 8

SP - 2049

EP - 2056

JO - ChemCatChem

JF - ChemCatChem

IS - 12

ER -

Recoverable Dendritic Phase-Transfer Catalysts that Contain (+)-Cinchonine-Derived Ammonium Salts

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