Allylsilylation and stannylation of 1,2-diketones using bifunctional allylsilane-allylstannane reagents via photoinduced electron transfer reaction

被引：9

作者：

Takuwa, A ^{[1
]}

Saito, H ^{[1
]}

Nishigaichi, Y ^{[1
]}

机构：

[1] Shimane Univ, Fac Sci & Engn, Dept Mat Sci, Matsue, Shimane 6908504, Japan

来源：

CHEMICAL COMMUNICATIONS | 1999年 / 19期

关键词：

D O I：

10.1039/a906620i

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Bifunctional allylsilane-allylstannane and allylstannane-allylstannane reagents react photochemically with 1,2-diketones to give alpha-ketohomoallyl alcohols having an allylsilane moiety and alpha-ketohomoally alcohols having an allylstannane moiety respectively in excellent yields, and the remaining allylstannane moiety further reacts effectively with another diketone in the presence of Mg(ClO4)(2) to afford a bis-alpha-ketohomoallyl alcohol.

引用

页码：1963 / 1964

页数：2

共 14 条

[1] STRUCTURES AND FRAGMENTATIONS OF ORGANOSILICON AND ORGANOTIN RADICAL CATIONS [J].

BUTCHER, E ;

RHODES, CJ ;

STANDING, M ;

DAVIDSON, RS ;

BOWSER, R .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1992, (09) :1469-1474

[2] ALLYLSTANNANES - SYNTHESIS, STRUCTURE, AND REACTIONS OF 2-METHYLENE-1,3-PROPANEDIYLBIS[TRIMETHYLSTANNANE] AND 2-METHYLENE-1,3-PROPANEDIYLBIS[TRIPHENYLSTANNANE] [J].

CHANDRASEKHAR, S ;

LATOUR, S ;

WUEST, JD ;

ZACHARIE, B .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (21) :3810-3813

[3] Radical allylations with trimethyl[2-[(tributylstannyl)methyl]-2-propenyl] silane or trimethy[2-[(triphenylstannyl)-methyl]-2-propenyl]silane [J].

Clive, DLJ ;

Paul, CC ;

Wang, ZR .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (20) :7028-7032

[4]

Fleming I., 1989, ORG REACTIONS, V37, P57

[5] ADDITION OF ORGANOSILANES WITH AROMATIC CARBONYL-COMPOUNDS VIA PHOTOINDUCED ELECTRON-TRANSFER IN THE PRESENCE OF MAGNESIUM PERCHLORATE [J].

FUKUZUMI, S ;

OKAMOTO, T ;

OTERA, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (12) :5503-5504

[6] Catalysis on electron transfer and the mechanistic insight into redox reactions [J].

Fukuzumi, S .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1997, 70 (01) :1-28

[7] A CONJUNCTIVE APPROACH TO THE SYNTHESIS OF FUNCTIONALIZED PIPERIDINES FROM IMINES [J].

KECK, GE ;

PALANI, A .

TETRAHEDRON LETTERS, 1993, 34 (20) :3223-3224

[8] SELECTIVE ELECTROPHILIC ADDITIONS OF MIXED BIFUNCTIONALIZED TRIMETHYLENEMETHANE DIANION SYNTHONS [J].

MAJETICH, G ;

NISHIDIE, H ;

ZHANG, Y .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (04) :453-457

[9] VERSATILE ROLES OF LEWIS-ACIDS IN THE REACTIONS OF ALLYLIC TIN-COMPOUNDS [J].

NISHIGAICHI, Y ;

TAKUWA, A ;

NARUTA, Y ;

MARUYAMA, K .

TETRAHEDRON, 1993, 49 (34) :7395-7426

[10] Stereoretentive introduction of (E)- and (Z)-γ-alkoxyallyl groups into carbonyl compounds via light-promoted reaction with γ-alkoxyallylstannanes [J].

Takuma, A ;

Nishigaichi, Y ;

Ebara, S ;

Iwamoto, H .

CHEMICAL COMMUNICATIONS, 1998, (17) :1789-1790

← 1 2 →