Synthetic and mechanistic studies of the cycloisomerization and cyclization/hydrosilylation of functionalized dienes catalyzed by cationic palladium(II) complexes

被引：142

作者：

Widenhoefer, RA ^{[1
]}

机构：

[1] Duke Univ, PM Gross Chem Lab, Durham, NC 27708 USA

来源：

ACCOUNTS OF CHEMICAL RESEARCH | 2002年 / 35卷 / 10期

关键词：

D O I：

10.1021/ar010040n

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

This Account describes the development and mechanistic study of the cycloisomerization and cyclization/hydrosilylation of functionalized dienes catalyzed by cationic palladium (II), complexes. These transformations are characterized by good functional group compatibility, high regio- and stereoselectivity, and low air- and moisture-sensitivity. Mechanistic studies of palladium phenanthroline-catalyzed diene cycloisomerization and cyclization/hydrosilylation established mechanisms involving C-C bond formation via intramolecular carbometalation of an alkyl olefin chelate complex, which was directly observed in the context of cyclization/hydrositylation.

引用

页码：905 / 913

页数：9

共 49 条

[21] Noyori R., 1994, ASYMMETRIC CATALYSIS
[22] SILYLCARBOCYCLIZATION REACTIONS CATALYZED BY RH AND RH-CO COMPLEXES
OJIMA, I
DONOVAN, RJ
SHAY, WR
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (16) : 6580 - 6582
[23] Transition metal-catalyzed carbocyclizations in organic synthesis
Ojima, I
Tzamarioudaki, M
Li, ZY
Donovan, RJ
[J]. CHEMICAL REVIEWS, 1996, 96 (02) : 635 - 662
[24] Ojima I., 2010, CATALYTIC ASYMMETRIC
[25] HYDROSILATION OF DIENES CATALYZED BY CP-ASTERISK-2NDCH(SIME(3))(2)
ONOZAWA, S
SAKAKURA, T
TANAKA, M
[J]. TETRAHEDRON LETTERS, 1994, 35 (44) : 8177 - 8180
[26] Palladium-catalyzed asymmetric diene cyclization/hydrosilylation employing functionalized silanes and disiloxanes
Pei, T
Widenhoefer, RA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (23) : 7639 - 7645
[27] Asymmetric diene cyclization/hydrosilylation/oxidation employing 1-tert-butyl-3,3-dimethyl-1,1-diphenyldisiloxane
Pei, T
Widenhoefer, RA
[J]. TETRAHEDRON LETTERS, 2000, 41 (40) : 7597 - 7600
[28] Use of pentamethyldisiloxane in the palladium-catalyzed cyclization/hydrosilylation of functionalized dienes
Pei, T
Widenhoefer, RA
[J]. ORGANIC LETTERS, 2000, 2 (10) : 1469 - 1471
[29] Direct observation of the conversion of a palladium 5-hexenyl chelate complex to a palladium cyclopentylmethyl complex
Perch, NS
Widenhoefer, RA
[J]. ORGANOMETALLICS, 2001, 20 (25) : 5251 - 5253
[30] Enantioselective diene cyclization/hydrosilylation catalyzed by optically active palladium bisoxazoline and pyridine-oxazoline complexes
Perch, NS
Pei, T
Widenhoefer, RA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (12) : 3836 - 3845

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