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Titolo:
Highly enantioselective reactions of configurationally labile alpha-thioorganolithiums using chiral bis(oxazoline)s via two different enantiodetermining steps
Autore:
Nakamura, S; Nakagawa, R; Watanabe, Y; Toru, T;
Indirizzi:
Nagoya Inst Technol, Dept Appl Chem, Showa Ku, Nagoya, Aichi 4668555, Japan Nagoya Inst Technol Nagoya Aichi Japan 4668555 goya, Aichi 4668555, Japan
Titolo Testata:
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
fascicolo: 46, volume: 122, anno: 2000,
pagine: 11340 - 11347
SICI:
0002-7863(20001122)122:46<11340:HEROCL>2.0.ZU;2-8
Fonte:
ISI
Lingua:
ENG
Soggetto:
STEREOSELECTIVE INTRAMOLECULAR CARBOLITHIATION; SUBSTITUTED ALKYLLITHIUM COMPOUNDS; CONJUGATE ADDITION-REACTIONS; OPTICALLY-ACTIVE EPOXIDES; TIN-LITHIUM EXCHANGE; ORGANOMETALLIC REAGENTS; ASYMMETRIC LITHIATION; KINETIC RESOLUTION; (-)-SPARTEINE-MEDIATED DEPROTONATION; PHENYLSELENOALKYLLITHIUM COMPOUNDS;
Tipo documento:
Review
Natura:
Periodico
Settore Disciplinare:
Life Sciences
Physical, Chemical & Earth Sciences
Citazioni:
123
Recensione:
Indirizzi per estratti:
Indirizzo: Toru, T Nagoya Inst Technol, Dept Appl Chem, Showa Ku, Nagoya, Aichi 4668555, Japan Nagoya Inst Technol Nagoya Aichi Japan 4668555 chi 4668555, Japan
Citazione:
S. Nakamura et al., "Highly enantioselective reactions of configurationally labile alpha-thioorganolithiums using chiral bis(oxazoline)s via two different enantiodetermining steps", J AM CHEM S, 122(46), 2000, pp. 11340-11347

Abstract

A cumene solution of alpha -stannyl benzyl phenyl sulfide was treated withn-BuLi and bis(oxazoline)-Pr-i: at -78 degreesC and subsequently with benzophenone to give the product with 99% ee. We confirmed that the reaction ofalpha -lithio benzyl phenyl sulfide proceeds through a dynamic kinetic resolution pathway. The enantioselective reactions of alpha -lithio benzyl 2-pyridyl sulfide gave the products with stereochemistry reverse to that obtained in the reaction of benzyl phenyl sulfide. We confirmed that this reaction proceeds through a dynamic thermodynamic resolution pathway in which thereaction with an electrophile proceeds faster than interconversion betweenthe diastereomeric complexes.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 25/02/20 alle ore 07:36:15