Novel concepts in directed biaryl synthesis.: Part 107.: Synthesis of enantiopure axially chiral C3-symmetric tripodal ligands and their application as catalysts in the asymmetric addition of dialkylzinc to aldehydes

被引：45

作者：

Bringmann, G ^{[1
]}

Pfeifer, RM ^{[1
]}

Rummey, C ^{[1
]}

Hartner, K ^{[1
]}

Breuning, M ^{[1
]}

机构：

[1] Univ Wurzburg, Inst Organ Chem, D-97074 Wurzburg, Germany

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 68卷 / 18期

关键词：

ENANTIOSELECTIVE ADDITION; NATURAL-PRODUCTS; AROMATIC-ALDEHYDES; CARBONYL-COMPOUNDS; LACTONE CONCEPT; REAGENTS; DIETHYLZINC; RECOGNITION; DERIVATIVES; COMPLEXES;

D O I：

10.1021/jo034697t

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The enantioselective synthesis of a novel-type C-3-symmetric tripodal ligand that is composed of a central mesitylene-derived core and three functionalized, axially chiral biaryl subunits is described. The triol (M,M,M)-3 is a suitable catalyst for the enantioselective addition of dialkylzinc to various aromatic aldehydes with asymmetric inductions of up to 98% ee.

引用

页码：6859 / 6863

页数：5

共 35 条

[1] Armstrong SK, 1999, SYNTHESIS-STUTTGART, P993
[2] Armstrong SK, 2000, SYNTHESIS-STUTTGART, P281
[3] A TETRAPHOS LIGAND WITH C3 SYMMETRY
BAKER, MJ
PRINGLE, PG
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (03) : 314 - 316
[4] TRIPODAL LIGANDS POSSESSING 6 CONVERGENT HYDROXYL-GROUPS A NOVEL FAMILY OF IRON SEQUESTERING AGENTS BASED ON O,O'-DIHYDROXYBIPHENYL SUBUNITS
BARET, P
BEGUIN, C
GAUDE, D
GELLON, G
MOURRAL, C
PIERRE, JL
SERRATRICE, G
FAVIER, A
[J]. TETRAHEDRON, 1994, 50 (07) : 2077 - 2094
[5] BILGER C, 1988, SYNTHESIS-STUTTGART, P902
[6] Novel concepts in directed biaryl synthesis, part 106.: Atropo-enantioselective synthesis of a C3-symmetric tripodal ligand with three axially chiral biaryl subunits
Bringmann, G
Breuning, M
Pfeifer, RM
Schreiber, P
[J]. TETRAHEDRON-ASYMMETRY, 2003, 14 (15) : 2225 - 2228
[7] Novel concepts in directed biaryl synthesis, part 102. The directed synthesis of axially chiral ligands, reagents, catalysts, and natural products through the 'lactone methodology'
Bringmann, G
Tasler, S
Pfeifer, RM
Breuning, M
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2002, 661 (1-2) : 49 - 65
[8] Novel concepts in directed biaryl synthesis, part 101. The lactone concept-a novel approach to the metal-assisted atroposelective construction of axially chiral biaryl systems
Bringmann, G
Breuning, M
Pfeifer, RM
Schenk, WA
Kamikawa, K
Uemura, M
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2002, 661 (1-2) : 31 - 47
[9] Stereoselective total synthesis of axially chiral natural products via biaryl lactones
Bringmann, G
Menche, D
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 2001, 34 (08) : 615 - 624
[10] Enantioselective addition of diethylzinc to aldehydes using novel axially chiral 2-aminomethyl-1-(2′-hydroxyphenyl)naphthalene catalysts
Bringmann, G
Breuning, M
[J]. TETRAHEDRON-ASYMMETRY, 1998, 9 (04) : 667 - 679

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