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Titolo:
The synthesis of 1-hydroxy phosphonates of high enantiomeric excess using sequential asymmetric reactions: titanium alkoxide-catalyzed P-C bond formation and kinetic resolution
Autore:
Rowe, BJ; Spilling, CD;
Indirizzi:
Univ Missouri, Dept Chem & Biochem, St Louis, MO 63121 USA Univ Missouri St Louis MO USA 63121 hem & Biochem, St Louis, MO 63121 USA
Titolo Testata:
TETRAHEDRON-ASYMMETRY
fascicolo: 12, volume: 12, anno: 2001,
pagine: 1701 - 1708
SICI:
0957-4166(20010716)12:12<1701:TSO1PO>2.0.ZU;2-1
Fonte:
ISI
Lingua:
ENG
Soggetto:
ALPHA-HYDROXY PHOSPHONATES; LI-BINOL COMPLEX; ORGANIC-CHEMISTRY; ENANTIOSELECTIVE HYDROLYSIS; CHEMOENZYMATIC SYNTHESIS; ASPERGILLUS-NIGER; ALLYLIC PHOSPHONATES; ACID ANALOGS; ENZYMES; ALDEHYDES;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Physical, Chemical & Earth Sciences
Citazioni:
47
Recensione:
Indirizzi per estratti:
Indirizzo: Spilling, CD Univ Missouri, Dept Chem & Biochem, 8001 Nat Bridge Rd, St Louis, MO 63121USA Univ Missouri 8001 Nat Bridge Rd St Louis MO USA 63121 121USA
Citazione:
B.J. Rowe e C.D. Spilling, "The synthesis of 1-hydroxy phosphonates of high enantiomeric excess using sequential asymmetric reactions: titanium alkoxide-catalyzed P-C bond formation and kinetic resolution", TETRAHEDR-A, 12(12), 2001, pp. 1701-1708

Abstract

Titanium alkoxide-catalyzed asymmetric phosphonylation of aldehydes yieldshydroxy phosphonates in moderate to good enantiomeric excess (e.e.s similar to 70%). The hydroxy phosphonates were acetylated and the acetates were subjected to enzyme-catalyzed kinetic resolution. The non-racemic acetates 2(predominantly (R)-enantiomer) were hydrolyzed with an (R)-enantiomer-selective lipase, resulting predominantly in the hydrolysis of the (R)-isomer (at 85% conversion) to give the alcohols 3 with high e.e. Alternatively, hydrolysis of the minor enantiomeric (S)-acetate to approximately 20% conversion left the enriched (R)-configured acetate with improved e.e. (> 90%). Themoderate enantio selectivities obtained in the catalytic P-C bond formation are enhanced during the enzymatic hydrolysis. Furthermore, availability of the non-racemic phosphonates permits the use of less selective enzymes, resulting in higher yields in comparison with the standard resolution of racemic materials. (C) 2001 Elsevier Science Ltd. All rights reserved.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 26/11/20 alle ore 13:45:10