2-Pyridylsilyl group: A useful multifunctional group in organic synthesis

被引：33

作者：

Itami, K ^{[1
]}

Yoshida, J

机构：

[1] Nagoya Univ, Res Ctr Mat Sci, Nagoya, Aichi 4648602, Japan

[2] JST, PRESTO, Kawaguchi, Saitama 3320012, Japan

[3] Kyoto Univ, Dept Synthet Chem & Biol Chem, Grad Sch Engn, Kyoto 6158510, Japan

来源：

SYNLETT | 2006年 / 02期

关键词：

2-pyridylsilyl group; removable directing group; phase tag;

D O I：

10.1055/s-2005-923611

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The utility of the 2-pyridylsilyl group as a multifunctional group in organic synthesis is described. The use of the 2-pyridylsilyl group as a removable directing group is a powerful synthetic strategy that circumvents the specificity-generality dilemma in mental-mediated organic synthesis. In addition, the utility of the 2-pyridylsilyl group as a phase tag for strategic separation and as a removable hydrophilic group for aqueous reactions is also described.

引用

页码：157 / 180

页数：24

共 234 条

[81] A Heck-type reaction involving carbon-heteroatom double bonds.: Rhodium(I)-catalyzed coupling of aryl halides with N-pyrazyl aldimines [J].

Ishiyama, T ;

Hartwig, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (48) :12043-12044

[82] Triarylethene-based extended π-systems:: Programmable synthesis and photophysical properties [J].

Itami, K ;

Ohashi, Y ;

Yoshida, J .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (07) :2778-2792

[83] Pyrimidine-core extended π-systems:: General synthesis and interesting fluorescent properties [J].

Itami, K ;

Yamazaki, D ;

Yoshida, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (47) :15396-15397

[84] Rapid construction of multisubstituted olefin structures using vinylboronate ester platform leading to highly fluorescent materials [J].

Itami, K ;

Tonogaki, K ;

Ohashi, Y ;

Yoshida, J .

ORGANIC LETTERS, 2004, 6 (22) :4093-4096

[85] Stereoselective synthesis of multisubstituted butadienes through directed Mizoroki-Heck reaction and homocoupling reaction of vinyl(2-pyridyl)silane [J].

Itami, K ;

Ushiogi, Y ;

Nokami, T ;

Ohashi, Y ;

Yoshida, JI .

ORGANIC LETTERS, 2004, 6 (21) :3695-3698

[86] Sequential assembly strategy for tetrasubstituted olefin synthesis using vinyl 2-pyrimidyl sulfide as a platform [J].

Itami, K ;

Mineno, M ;

Muraoka, N ;

Yoshida, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (38) :11778-11779

[87] Catalytic intermolecular Pauson-Khand-type reaction: Strong directing effect of pyridylsilyl and pyrimidylsilyl groups and isolation of Ru complexes relevant to catalytic reaction [J].

Itami, K ;

Mitsudo, K ;

Fujita, K ;

Ohashi, Y ;

Yoshida, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (35) :11058-11066

[88] Iron-catalyzed cross-coupling of alkenyl sulfides with Grignard reagents [J].

Itami, K ;

Higashi, S ;

Mineno, M ;

Yoshida, J .

ORGANIC LETTERS, 2005, 7 (07) :1219-1222

[89] Diversity-oriented synthesis of tamoxifen-type tetrasubstituted olefins [J].

Itami, K ;

Kamei, T ;

Yoshida, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (48) :14670-14671

[90] Palladium-catalyzed rearrangement/arylation of 2-allyloxypyridine leading to the synthesis of N-substituted 2-pyridones [J].

Itami, K ;

Yamazaki, D ;

Yoshida, J .

ORGANIC LETTERS, 2003, 5 (12) :2161-2164

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