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Titolo:
ASYMMETRIC OLEFINATION USING OPTICALLY-AC TIVE PHOSPHORUS REAGENTS
Autore:
TANAKA K; FUJI K;
Indirizzi:
UNIV SHIZUOKA,SCH PHARMACEUT SCI,52-1 YADA SHIZUOKA 4228002 JAPAN KYOTO UNIV,INST CHEM RES UJI KYOTO 6110011 JAPAN
Titolo Testata:
Yuki Gosei Kagaku Kyokaishi
fascicolo: 6, volume: 56, anno: 1998,
pagine: 521 - 531
SICI:
0037-9980(1998)56:6<521:AOUOTP>2.0.ZU;2-0
Fonte:
ISI
Lingua:
JPN
Soggetto:
WADSWORTH-EMMONS REACTION; DYNAMIC KINETIC RESOLUTION; HORNER-WITTIG REACTION; HIGH ENANTIOMERIC PURITY; PHOSPHINE OXIDES; ALPHA-ALKYL; STEREOSELECTIVE SYNTHESIS; STABILIZED CARBANIONS; SELECTIVE SYNTHESIS; ORGANIC-SYNTHESIS;
Keywords:
ASYMMETRIC OLEFINATION; CHIRAL PHOSPHORUS REAGENT; KINETIC RESOLUTION; DESYMMETRIZATION; BINOL; 8-PHENYLMENTHYL AUXILIARY; HORNER-WADSWORTH-EMMONS REACTION; E/Z STEREOCHEMISTRY;
Tipo documento:
Review
Natura:
Periodico
Settore Disciplinare:
Science Citation Index Expanded
Citazioni:
111
Recensione:
Indirizzi per estratti:
Citazione:
K. Tanaka e K. Fuji, "ASYMMETRIC OLEFINATION USING OPTICALLY-AC TIVE PHOSPHORUS REAGENTS", Yuki Gosei Kagaku Kyokaishi, 56(6), 1998, pp. 521-531

Abstract

The Wittig reaction and its variants produce no sp(3) stereocenter, nevertheless asymmetric transformation from achiral carbonyl compounds can be achieved by using optically active phosphorus reagents. These approaches are based on three different methodologies, kinetic resolution and discrimination of either pi-face of carbonyl or enantiotopic carbonyl groups in the symmetrical molecules. A variety of phosphorus reagents has been reported and used for these transformations. Among theHorner-Wadsworth-Emmons (HWE) type reagents, those possessing 8-phenylmenthyl or binaphthyl groups as a chiral auxiliary exert high level of asymmetric induction. For example, the HWE reagent of binaphthyl group effectively discriminated the carbonyl face giving dissymmetric olefins, and differentiated enantiotopic carbonyls of meso-alpha-diketones to afford the Z- and E-olefins with high optical yield. This discrimination was successfully applied to the practical one-pot procedure for optically active allenic compounds as well as the construction of the fused ring systems through the intramolecular HWE reaction.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 02/12/20 alle ore 06:43:47