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Synthesis of P,P-heterotopic binaphthyldiphosphanes (BINAPP') devoid of C2 symmetry from 2,2'-binaphthol

Gladiali, Serafino Gabriele and Dore, Antonio and Fabbri, Davide and Medici, Serenella and Pirri, Giovanna and Pulacchini, Sonia (2000) Synthesis of P,P-heterotopic binaphthyldiphosphanes (BINAPP') devoid of C2 symmetry from 2,2'-binaphthol. European Journal of Organic Chemistry, Vol. 2000 (16), p. 2861-2865. eISSN 1099-0690. Article.

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DOI: 10.1002/1099-0690(200008)2000:16<2861::AID-EJOC2861>3.0.CO;2-V

Abstract

The introduction of two nonequivalent diarylphosphanyl substituents into the 2- and 2'-positions of 1,1'-binaphthalene has been successfully accomplished in four steps from 1,1'-binaphthalene-2,2'-diol (BINOL) through conversion into the ditriflate followed by sequential substitution of triflate groups mediated by palladium or nickel catalysts. The selective monosubstitution of the triflate has been achieved by introducing the first phosphorated substituent in the form of phosphane oxide through a Pd-catalyzed reaction. The otolyl- substituted diphosphane 4c is a chiral inducer that is more efficient than BINAP both in the Rh-catalyzed asymmetric hydrogenation of acetamido acrylic acid derivatives and in the Pd-catalyzed allylic alkylation of 1,3-diphenylprop- 2-enyl acetate (85% ee).

Item Type:Article
ID Code:5285
Status:Published
Refereed:Yes
Uncontrolled Keywords:Atropisomerism, phosphanes, asymmetric catalysis, hydrogenations, rhodium, alkylations
Subjects:Area 03 - Scienze chimiche > CHIM/04 Chimica industriale
Divisions:001 Università di Sassari > 01 Dipartimenti > Chimica
002 Altri enti e centri di ricerca del Nord Sardegna > CNR-Consiglio Nazionale delle Ricerche > Istituto di chimica biomolecolare, Sassari
Publisher:Wiley
eISSN:1099-0690
Deposited On:10 Jan 2011 16:38

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