Aryl ferrophites - A new class of ligands for asymmetric catalysis

被引：31

作者：

Albrow, Victoria E. ^{[1
]}

Blake, Alexander J. ^{[1
]}

Fryatt, Ross ^{[1
]}

Wilson, Claire ^{[1
]}

Woodward, Simon ^{[1
]}

机构：

[1] Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2006年 / 2006卷 / 11期

关键词：

ferrocenyl ligands; P ligands; phosphites; asymmetric catalysis;

D O I：

10.1002/ejoc.200600071

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Enantiopure lithiated 1,2-ferrocenes, [CpFe{1,2-eta(5)-C5H3(Ar)-(Li)}] (Ar = Ph, 4-CF3C6H4, 1-C10H7) react readily with PhOP(OR)(2) to yield [CpFe{1,2-eta(5)-C5H3(Ar)P(OR)(2)}] (R = Ph, 1, 1'-biphenyl-based, 1, 1'-binaphthyl-based) efficiently. Traditional routes to these species, involving the use of chlorophosphites CIP(OR)(2) were found to be ineffective. These "ferrophite" ligands have been characterised by X-ray crystallography (4 examples) and shown to be effective in both nickel-catalysed addition of AlMe3 to PhCHO (up to 77% ee) and copper(I)-catalysed additions of organoaluminium reagents to enones (up to 92% ee).

引用

页码：2549 / 2557

页数：9

共 26 条

[1] ALBROW V, IN PRESS INORG CHIM
[2] Highly enantioselective copper(I)-phosphoramidite-catalysed additions of organoaluminium reagents to enones
Alexakis, A
Albrow, V
Biswas, K
d'Augustin, M
Prieto, O
Woodward, S
[J]. CHEMICAL COMMUNICATIONS, 2005, (22) : 2843 - 2845
[3] Alexakis A, 2000, EUR J ORG CHEM, V2000, P4011, DOI 10.1002/1099-0690(200012)2000:24<4011::AID-EJOC4011>3.0.CO
[4] 2-D
[5] Dabbling with air-stable organoaluminum species
Biswas, K
Chapron, A
Cooper, T
Fraser, PK
Novak, A
Prieto, O
Woodward, S
[J]. PURE AND APPLIED CHEMISTRY, 2006, 78 (02) : 511 - 518
[6] Expedient synthesis of β,β-disubstituted α-methylenepropionates
Biswas, K
Börner, C
Gimeno, J
Goldsmith, PJ
Ramazzotti, D
So, ALK
Woodward, S
[J]. TETRAHEDRON, 2005, 61 (06) : 1433 - 1442
[7] Highly selective Negishi cross-coupling reaction of a zinc-metallated ferrocenyl p-tolyl sulfoxide:: New chiral ferrocene-based quinone ligands
Cotton, HK
Huerta, FF
Bäckvall, JE
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (15) : 2756 - 2763
[8] Phosphoramidites: Marvellous ligands in catalytic asymmetric conjugate addition
Feringa, BL
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (06) : 346 - 353
[9] Origin of enantioselectivity in asymmetric hydrovinylations catalyzed by phosphoramidite nickel catalysts:: An experimentally supported density functional study
Hölscher, M
Franciò, G
Leitner, W
[J]. ORGANOMETALLICS, 2004, 23 (23) : 5606 - 5617
[10] Expanding Pd-catalyzed C-N bond-forming processes: The first amidation of aryl sulfonates, aqueous amination, and complementarity with Cu-catalyzed reactions
Huang, XH
Anderson, KW
Zim, D
Jiang, L
Klapars, A
Buchwald, SL
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (22) : 6653 - 6655

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