Rhodium-catalyzed asymmetric 1,4-addition of organoboron reagents to 5,6-dihydro-2(1H)-pyridinones.: Asymmetric synthesis of 4-aryl-2-piperidinones

被引：161

作者：

Senda, T ^{[1
]}

Ogasawara, M ^{[1
]}

Hayashi, T ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Sci, Dept Chem, Kyoto 6068502, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2001年 / 66卷 / 21期

关键词：

D O I：

10.1021/jo0103930

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Catalytic asymmetric synthesis of 4-aryl-2-piperidinones was realized for the first time by asymmetric 1,4-addition of arylboron reagents to 5,6-dihydro-2(1H)-pyridinones in the presence of a chiral bisphosphine-rhodium catalyst. In the reaction introducing 4-fluorophenyl group, the use of 4-fluorophenylboroxine and 1 equiv (to boron) of water at 40 degreesC gave the highest yield of the arylation product with high enantioselectivity (98% ee). The (R)-4-(4-fluorophenyl)-2-piperidinone obtained here is a key intermediate for the synthesis of (-)-Paroxetine.

引用

页码：6852 / 6856

页数：5

共 28 条

[11] Synthesis and pharmacology of the baclofen homologues 5-amino-4-(4-chlorophenyl)pentanoic acid and the R- and S-enantiomers of 5-amino-3-(4-chlorophenyl)pentanoic acid [J].

Karla, R ;

Ebert, B ;

Thorkildsen, C ;

Herdeis, C ;

Johansen, TN ;

Nielsen, B ;

Krogsgaard-Larsen, P .

JOURNAL OF MEDICINAL CHEMISTRY, 1999, 42 (11) :2053-2059

[12]

Krause N, 2001, SYNTHESIS-STUTTGART, P171

[13] ORGANIC COMPOUNDS OF BORON [J].

LAPPERT, MF .

CHEMICAL REVIEWS, 1956, 56 (05) :959-1064

[14] BINAP - AN EFFICIENT CHIRAL ELEMENT FOR ASYMMETRIC CATALYSIS [J].

NOYORI, R ;

TAKAYA, H .

ACCOUNTS OF CHEMICAL RESEARCH, 1990, 23 (10) :345-350

[15] Asymmetric conjugate 1,4-addition of arylboronic acids to α,β-unsaturated esters catalyzed by rhodium(I)/(S)-binap [J].

Sakuma, S ;

Sakai, M ;

Itooka, R ;

Miyaura, N .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (19) :5951-5955

[16]

Sibi MP, 2000, TETRAHEDRON, V56, P8033

[17]

TAKAYA H, 1989, ORG SYNTH, V67, P20

[18] PRACTICAL SYNTHESIS OF (R)-2,2' OR (S)-2,2'-BIS(DIARYLPHOSPHINO)-1,1'-BINAPHTHYLS (BINAPS) [J].

TAKAYA, H ;

MASHIMA, K ;

KOYANO, K ;

YAGI, M ;

KUMOBAYASHI, H ;

TAKETOMI, T ;

AKUTAGAWA, S .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (05) :629-635

[19] Rhodium-catalyzed asymmetric 1,4-addition of arylboron reagents to α,β-unsaturated esters [J].

Takaya, Y ;

Senda, T ;

Kurushima, H ;

Ogasawara, M ;

Hayashi, T .

TETRAHEDRON-ASYMMETRY, 1999, 10 (20) :4047-4056

[20] Rhodium-catalyzed asymmetric 1,4-addition of arylboron compounds generated in situ from aryl bromides [J].

Takaya, Y ;

Ogasawara, M ;

Hayashi, T .

TETRAHEDRON LETTERS, 1999, 40 (38) :6957-6961

← 1 2 3 →