Palladium-catalyzed regio- and diastereoselective allylic alkylation with azlactones using triphenylarsine

被引：17

作者：

Kawatsura, Motoi ^{[1
]}

Ikeda, Daiji

Ishii, Tamiko

Komatsu, Yuji

Uenishi, Junichi

机构：

[1] Tottori Univ, Fac Engn, Dept Mat Sci, Tottori 6808552, Japan

[2] Kyoto Pharmaceut Univ, Kyoto 6078412, Japan

来源：

SYNLETT | 2006年 / 15期

关键词：

palladium catalysis; triphenylarsine; regioselectivity; diastereoselectivity; alkylations;

D O I：

10.1055/s-2006-950400

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The palladium-catalyzed regio- and diastereoselective allylic alkylation of (R)-2-acetoxy-4-phenyl-3-butene with azlactones using AsPh3 successfully occurred. The stereochemistries were highly controlled, and the reaction produced a coupling product which possessed vicinal chiral quaternary and tertiary carbon centers.

引用

页码：2435 / 2438

页数：4

共 34 条

[11] Synthesis of β-substituted α-amino acids with use of iridium-catalyzed asymmetric allylic substitution [J].

Kanayama, T ;

Yoshida, K ;

Miyabe, H ;

Kimachi, T ;

Takemoto, Y .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (16) :6197-6201

[12]

Kazmaier U, 2000, ANGEW CHEM INT EDIT, V39, P802, DOI 10.1002/(SICI)1521-3773(20000218)39:4<802::AID-ANIE802>3.0.CO

[13]

2-Y

[14] Asymmetric allylation of unsymmetrical 1,3-diketones using a BINAP-palladium catalyst [J].

Kuwano, R ;

Uchida, K ;

Ito, Y .

ORGANIC LETTERS, 2003, 5 (12) :2177-2179

[15] Catalytic asymmetric allylation of prochiral nucleophiles, α-acetamido-β-ketoesters [J].

Kuwano, R ;

Ito, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (13) :3236-3237

[16] Enantioselective construction of quaternary α-carbon centers on α-amino phosphonates via catalytic asymmetric allylation [J].

Kuwano, R ;

Nishio, R ;

Ito, Y .

ORGANIC LETTERS, 1999, 1 (06) :837-839

[17] Substrate-controlled palladium-catalyzed allylic alkylations of chelated enolates - Scope and limitations [J].

Lindner, T ;

Kazmaier, U .

ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (11-13) :1687-1695

[18] Recent developments in the catalytic asymmetric synthesis of α- and β-amino acids [J].

Ma, JA .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (36) :4290-4299

[19] PHERMONE SYNTHESIS .53. SYNTHESIS AND ABSOLUTE STEREOCHEMISTRY OF SERRICORNIN [(4S, 6S, 7S)-4,6-DIMETHYL-7-HYDROXY-3-NONANONE] - THE SEX-PHEROMONE OF THE CIGARETTE BEETLE [J].

MORI, K ;

NOMI, H ;

CHUMAN, T ;

KOHNO, M ;

KATO, K ;

NOGUCHI, M .

TETRAHEDRON, 1982, 38 (24) :3705-3711

[20] P-chirogenic diaminophosphine oxide: A new class of chiral phosphorus ligands for asymmetric catalysis [J].

Nemoto, T ;

Matsumoto, T ;

Masuda, T ;

Hitomi, T ;

Hatano, K ;

Hamada, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (12) :3690-3691

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