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Titolo:
ISOPINOCAMPHEYLHALOBORANE-METHYL SULFIDE AS HYDROBORATING AND STEREOSELECTIVE REDUCING AGENT
Autore:
CHA JS; MIN SJ; KIM JM; KWON OO; KIM EJ;
Indirizzi:
YEUNGNAM UNIV,DEPT CHEM KYONGSAN 712749 SOUTH KOREA
Titolo Testata:
Bulletin of the Korean Chemical Society
fascicolo: 1, volume: 16, anno: 1995,
pagine: 37 - 42
SICI:
0253-2964(1995)16:1<37:ISAHAS>2.0.ZU;2-R
Fonte:
ISI
Lingua:
ENG
Soggetto:
HIGH ENANTIOMERIC PURITY; ALKALI-METAL HYDRIDES; CHIRAL SYNTHESIS; SELECTIVE REDUCTIONS; ASYMMETRIC REDUCTION; CONVENIENT PROCEDURES; ADDITION-COMPOUNDS; PROCHIRAL KETONES; ALKENES; ALKYNES;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Science Citation Index Expanded
Citazioni:
38
Recensione:
Indirizzi per estratti:
Citazione:
J.S. Cha et al., "ISOPINOCAMPHEYLHALOBORANE-METHYL SULFIDE AS HYDROBORATING AND STEREOSELECTIVE REDUCING AGENT", Bulletin of the Korean Chemical Society, 16(1), 1995, pp. 37-42

Abstract

Reactions of alkenes and alkynes with the recently discovered isopinocampheylhaloborane-methyl sulfide (IpcBHX.SMe(2), X=Cl, Br, I) were investigated in detail in order to establish their usefulness as hydroborating agents. The reagents readily hydroborated alkenes at 50 degreesC and alkynes at 25 degrees C with excellent regioselectivity in placing the boron atom exclusively at the less hindered carbon atom. Especially, the selectivity achieved by the iodo derivative reaches essentially 100%. In addition to that, IpcBHX.SMe(2) was applied to the reduction of cyclic ketones to examine its stereoselectivity. The halogen substituent in these reagents plays an important role in the stereoselective reduction. The stereoselectivity increased dramatically with increasing steric size of the substituent. Finally, the iodo derivative achieved highly stereoselective reduction, such selectivity being comparable to that previously achieved with trialkylborohydrides.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 20/10/20 alle ore 05:05:45