Ruthenium Catalyzed Cycloisomerization of Silicon-Tethered 1,7-Enynes To Give Exocyclic 1,3-Dienes

被引：18

作者：

Kaminsky, Lauren ^{[1
]}

Clark, Daniel A. ^{[1
]}

机构：

[1] Syracuse Univ, Dept Chem, Ctr Sci & Technol 1 014, Syracuse, NY 13244 USA

来源：

ORGANIC LETTERS | 2014年 / 16卷 / 20期

基金：

美国国家科学基金会;

关键词：

STEREOSELECTIVE-SYNTHESIS; 5+2 CYCLOADDITIONS; INTERNAL ALKYNES; ENYNE CYCLOISOMERIZATIONS; SKELETAL REORGANIZATION; TRANS-SILYLVINYLATION; BOND FORMATION; ATOM ECONOMY; CYCLIZATION; METATHESIS;

D O I：

10.1021/ol5026926

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The cycloisomerization of vinyl silicon-tethered 1,7-enynes has been accomplished using catalytic Cp*Ru(COD)Cl. The products possess a new silane moiety and trisubstituted alkenes as part of the diene system. The reaction scope includes aryl, alkyl, vinyl, and cyclopropyl alkyne functionalities. Silicon was found not to be a mandatory component of the tether. The utility of the products was demonstrated through manipulation of the vinyl silane and Diels-Alder chemistry.

引用

页码：5450 / 5453

页数：4

共 57 条

[1]

[Anonymous], 2004, METAL CATALYZED CROS, V1

[2] The behavior of 1,n-enynes in the presence of transition metals [J].

Aubert, C ;

Buisine, O ;

Malacria, M .

CHEMICAL REVIEWS, 2002, 102 (03) :813-834

[3] The formation and stabillity of spiro-compounds. Part I. Spiro-compounds from cyclo-hexane. [J].

Beesley, RM ;

Ingold, CK ;

Thorpe, JF .

JOURNAL OF THE CHEMICAL SOCIETY, 1915, 107 :1080-1106

[4]

Buisine O, 2001, CHEM-EUR J, V7, P3517, DOI 10.1002/1521-3765(20010817)7:16<3517::AID-CHEM3517>3.0.CO

[5]

2-V

[6] Skeletal reorganization of enynes to 1-vinylcycloalkenes catalyzed by GaCl3 [J].

Chatani, N ;

Inoue, H ;

Kotsuma, T ;

Murai, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (35) :10294-10295

[7] HIGHLY SELECTIVE SKELETAL REORGANIZATION OF 1,6-ENYNE AND 1,7-ENYNE TO 1-VINYLCYCLOALKENES CATALYZED BY [RUCL2(CO)(3)](2) [J].

CHATANI, N ;

MORIMOTO, T ;

MUTO, T ;

MURAI, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (13) :6049-6050

[8] Total Synthesis of (±)-Gelsemoxonine [J].

Diethelm, Stefan ;

Carreira, Erick M. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (23) :8500-8503

[9] Enyne metathesis (enyne bond reorganization) [J].

Diver, ST ;

Giessert, AJ .

CHEMICAL REVIEWS, 2004, 104 (03) :1317-1382

[10] Asymmetric cycloisomerization of 1,6-and 1,7-enynes by transition-metal catalysts [J].

Fairlamb, IJS .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (09) :1048-1052

← 1 2 3 4 5 6 →