Highly enantioselective synthesis of pseudo-C2-symmetric axially chiral biaryl diphosphines via rhodium-catalyzed double [2+2+2] cycloaddition

被引：37

作者：

Doherty, Simon ^{[1
]}

Smyth, Catherine H. ^{[1
]}

Harrington, Ross W. ^{[1
]}

Clegg, William ^{[1
]}

机构：

[1] Newcastle Univ, Sch Chem, Newcastle Upon Tyne NE1 7RU, Tyne & Wear, England

来源：

ORGANOMETALLICS | 2008年 / 27卷 / 19期

基金：

英国工程与自然科学研究理事会;

关键词：

D O I：

10.1021/om800755x

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Cationic rhodium complexes based on (R)-BINAP catalyze the sequential double [2 + 2 + 2] cycloaddition between 1,4-bis(diphenylphosphinoyl)buta-1,3-diyne and an internal 2,n-diyne followed by its terminal counterpart in an operationally straightforward procedure to afford pseudo-C-2-symmetric axially chiral biaryl diphosphines in good yield and with exceptionally high enantioselectivity.

引用

收藏

页码：4837 / 4840

页数：4

相关论文

共 52 条

[1] Convenient and direct preparation of tertiary phosphines via nickel-catalysed cross-coupling [J].

Ager, DJ ;

East, MB ;

Eisenstadt, A ;

Laneman, SA .

CHEMICAL COMMUNICATIONS, 1997, (24) :2359-2360

[2] Asymmetric catalysis of ene reactions with trifluoropyruvate catalyzed by dicationic palladium(II) complexes [J].

Aikawa, K ;

Kainuma, S ;

Hatano, M ;

Mikami, K .

TETRAHEDRON LETTERS, 2004, 45 (01) :183-185

[3]

[Anonymous], PHOSPHORUS LIGANDS A

[4] Synthesis of tetra-ortho-substituted, phosphorus-containing and carbonyl-containing biaryls utilizing a diels-alder approach [J].

Ashburn, Bradley O. ;

Carter, Rich G. ;

Zakharov, Lev N. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (29) :9109-9116

[5] Diels-Alder approach to polysubstituted biaryls: Rapid entry to tri- and tetra-ortho-substituted phosphorus-containing biaryls [J].

Ashburn, Bradley O. ;

Carter, Rich G. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (40) :6737-6741

[6] Modified BINAP: The how and the why [J].

Berthod, M ;

Mignani, G ;

Woodward, G ;

Lemaire, M .

CHEMICAL REVIEWS, 2005, 105 (05) :1801-1836

[7] Atroposelective synthesis of axially chiral biaryl compounds [J].

Bringmann, G ;

Mortimer, AJP ;

Keller, PA ;

Gresser, MJ ;

Garner, J ;

Breuning, M .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (34) :5384-5427

[8]

CAI D, 1998, ORG SYNTH, V76, P6

[9] [2+2+2] cycloaddition reactions catalyzed by transition metal complexes [J].

Chopade, Pramod R. ;

Louie, Janis .

ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (16-17) :2307-2327

[10] Lewis acid platinum complexes of conformationally flexible NUPHOS diphosphines: Highly efficient catalysts for the carbonyl-ene reaction [J].

Doherty, S ;

Goodrich, P ;

Hardacre, C ;

Luo, HK ;

Nieuwenhuyzen, M ;

Rath, RK .

ORGANOMETALLICS, 2005, 24 (24) :5945-5955

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