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Titolo:
Stereospecific 1,3-migration of an Fe(CO)(3) group on acyclic conjugated polyenes: Application to remote and iterative asymmetric induction
Autore:
Takemoto, Y; Ishii, K; Ibuka, T; Miwa, Y; Taga, T; Nakao, S; Tanaka, T; Ohishi, H; Kai, Y; Kanehisa, N;
Indirizzi:
Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan Kyoto Univ Kyoto Japan 6068501 aceut Sci, Sakyo Ku, Kyoto 6068501, Japan Osaka Univ, Grad Sch Pharmaceut Sci, Suita, Osaka 5650871, Japan Osaka Univ Suita Osaka Japan 5650871 eut Sci, Suita, Osaka 5650871, Japan Osaka Univ Pharmaceut Sci, Takatsuki, Osaka 5691094, Japan Osaka Univ Pharmaceut Sci Takatsuki Osaka Japan 5691094 ka 5691094, Japan Osaka Univ, Grad Sch Engn, Mat Chem Dept Mat Chem, Suita, Osaka 5650871, Japan Osaka Univ Suita Osaka Japan 5650871 at Chem, Suita, Osaka 5650871, Japan
Titolo Testata:
JOURNAL OF ORGANIC CHEMISTRY
fascicolo: 18, volume: 66, anno: 2001,
pagine: 6116 - 6123
SICI:
0022-3263(20010907)66:18<6116:S1OAFG>2.0.ZU;2-4
Fonte:
ISI
Lingua:
ENG
Soggetto:
PI-ALLYLTRICARBONYLIRON LACTONE; DIASTEREOSELECTIVE 1,2-NUCLEOPHILIC ADDITION; CATALYTIC ENANTIOSELECTIVE ALKYLATION; DIENE-TRICARBONYLIRON COMPLEX; EXCELLENT CHIRAL INTRODUCTION; ALDOL CONDENSATION-REACTIONS; SUGAR ORTHO ESTER; STEREOSELECTIVE SYNTHESIS; (DIENE)FE(CO)(3) COMPLEXES; ORGANOIRON METHODOLOGY;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Life Sciences
Physical, Chemical & Earth Sciences
Citazioni:
62
Recensione:
Indirizzi per estratti:
Indirizzo: Takemoto, Y Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan Kyoto Univ Kyoto Japan 6068501 akyo Ku, Kyoto 6068501, Japan
Citazione:
Y. Takemoto et al., "Stereospecific 1,3-migration of an Fe(CO)(3) group on acyclic conjugated polyenes: Application to remote and iterative asymmetric induction", J ORG CHEM, 66(18), 2001, pp. 6116-6123

Abstract

The stereochemical outcome of the 1,3- and 1,5-migration of an Fe(CO)(3) group on (acyclic polyene)Fe(CO)3 complexes and their application to stereoselective construction of remote and contiguous stereogenic centers are described. Treatment of the [(eta (4)-4-7)triene]Fe(CO)(3) complexes 1a-d bearing an electron-withdrawing group on the terminal position of an uncomplexedolefin with a base such as KN(SiMe3)(2) (KHMDS) and LiCH2CN induced the 1,3-migration reaction of the Fe(CO)3 group, giving the [(eta (4)-2-5)triene]Fe(CO)(3) complexes 2a-d in moderate to good yields, depending on the electron-withdrawing groups. From an experiment using the chiral (trienenitril)Fe(CO)3 complex 5, it is revealed that the 1,3-migration proceeds with inversion of configuration. Similarly, the 1,5-migration reaction of the [(eta (4)-6-9)tetraenone]Fe(CO)(3) complexes 9 occurred with a catalytic amount ofKHMDS, giving the [(eta (4)-2-5)tetraenone]Fe(CO)(3) complexes 10 with retention of configuration. Furthermore, we have succeeded in the first regio-and stereoselective nucleophilic substitution of the (3,5-diene-1,2-diol) Fe(CO)(3) complexes (15 --> 24a-h) with various nucleophiles via the ortho esters 21. By using iterative manipulation of the above two reactions, remote stereocontrol of the terminal substituents on acyclic polyene (9 --> 12)and construction of contiguous stereogenic centers (19, 28) have been achieved.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 30/10/20 alle ore 10:02:11