Novel carbonyl-dependent regioselective allylation via diethylzinc-mediated umpolung of π-allylpalladium

被引：24

作者：

Kimura, M ^{[1
]}

Ogawa, Y ^{[1
]}

Shimizu, M ^{[1
]}

Sueishi, M ^{[1
]}

Tanaka, S ^{[1
]}

Tamaru, Y ^{[1
]}

机构：

[1] Nagasaki Univ, Fac Engn, Dept Appl Chem, Nagasaki 8528521, Japan

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 38期

关键词：

D O I：

10.1016/S0040-4039(98)01448-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Palladium-catalyzed allylation of carbonyls (1.1 - 1.5 mmol) with allylic esters 3a-d (1 mmol) in the presence of Pd(PPh3)(4) (0.05 mmol) and Et2Zn (2.4 mmol) in THF at room temperature shows marked carbonyl-dependent regioselectivity, providing alpha-allylation products 5 with benzaldehyde and gamma-allylation products 6 with acetone and ethyl acetate. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：6903 / 6906

页数：4

共 8 条

[1]

HOPPE D, 1986, ANGEW CHEM, V98, P171

[2] REAGENT-CONTROLLED ENANTIOSELECTIVE HOMOALDOL REACTION WITH CHIRAL 1-OXYALLYLLITHIUM DERIVATIVES - ENANTIO-DIVERGENT TUNING BY ACHIRAL TITANIUM REAGENTS [J].

KRAMER, T ;

HOPPE, D .

TETRAHEDRON LETTERS, 1987, 28 (43) :5149-5152

[3] Unique regio- and stereoselectivity in the allylation of benzaldehyde with 2-substituted allylzincs generated by umpolung of π-allylpalladium [J].

Shimizu, M ;

Kimura, M ;

Tanaka, S ;

Tamaru, Y .

TETRAHEDRON LETTERS, 1998, 39 (07) :609-612

[4]

Streitwieser A., 1992, INTRO ORGANIC CHEM

[5] Unique reaction behavior of organozincs toward pi-allylpalladium complexes: Palladium catalyzed synthesis of unsymmetrical ketones and umpolung of pi-allylpalladium [J].

Tamaru, Y .

JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 1995, 53 (12) :1102-1113

[6] HIGHLY STEREOSELECTIVE ALLYLATION OF BENZALDEHYDE - GENERATION OF A STEREOCHEMICALLY DEFINED ALLYLZINC SPECIES FROM A PI-ALLYLPALLADIUM INTERMEDIATE AND DIETHYLZINC [J].

TAMARU, Y ;

TANAKA, A ;

YASUI, K ;

GOTO, S ;

TANAKA, S .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (07) :787-789

[7] PALLADIUM-MEDIATED INTRAMOLECULAR C-N BOND FORMATION BETWEEN TERTIARY-AMINES AND ALKENES [J].

VANDERSCHAAF, PA ;

SUTTER, JP ;

GRELLIER, M ;

VANMIER, GPM ;

SPEK, AL ;

VANKOTEN, G ;

PFEFFER, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (12) :5134-5144

[8] USE OF PI-ALLYLPALLADIUM AS A NUCLEOPHILE VIA AN ALKYL-ALLYL EXCHANGE-REACTION WITH ALKYLZINC [J].

YASUI, K ;

GOTO, Y ;

YAJIMA, T ;

TANISEKI, Y ;

FUGAMI, K ;

TANAKA, A ;

TAMARU, Y .

TETRAHEDRON LETTERS, 1993, 34 (47) :7619-7622

← 1 →