Resolution of BIPHEP on Rh with a chiral diene auxiliary

被引:23
作者
Faller, J. W. [1 ]
Wilt, Jeremy C. [1 ]
机构
[1] Yale Univ, Dept Chem, New Haven, CT 06520 USA
关键词
asymmetric catalysis; resolution; chiral induction;
D O I
10.1016/j.jorganchem.2005.09.050
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Resolution of the atropisomeric chiral BIPHEP ligand on Rh has been achieved with the aid of 2-(4-tert-butyl-phenyl)-8-methoxy-1,8-dimethyl-bicyclo[2,2,2]octa-2,5-diene, a chiral chelating diene ligand. The diene complex 3 containing an (S)-BIPHEP ligand was found to be configurationally stable in CDCl3 solution at RT. Conversion of the diene complex 3 to a dicarbonyl Rh complex 4 that had a barrier of 25.0 kcal/mol for atropisomerization of the BIPHEP ligand. Preliminary studies of the use of the resolved complex 3 for catalysis are presented. (c) 2005 Elsevier B.V. All rights reserved.
引用
收藏
页码:2207 / 2212
页数:6
相关论文
共 51 条
[1]   COMPLETION AND REFINEMENT OF CRYSTAL-STRUCTURES WITH SIR92 [J].
ALTOMARE, A ;
CASCARANO, G ;
GIACOVAZZO, C ;
GUAGLIARDI, A .
JOURNAL OF APPLIED CRYSTALLOGRAPHY, 1993, 26 (pt 3) :343-350
[2]   Asymmetric catalysis with the normally unresolvable, conformationally dynamic 2,2′-bis(diphenylphosphino)-1,1′-biphenyl (biphep) [J].
Becker, JJ ;
White, PS ;
Gagné, MR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (38) :9478-9479
[3]   Synthesis of chiral binaphthalenes using the asymmetric Suzuki reaction [J].
Cammidge, AN ;
Crépy, KVL .
TETRAHEDRON, 2004, 60 (20) :4377-4386
[4]   Asymmetric synthesis of axially chiral biaryls by nickel-catalyzed grignard cross-coupling of dibenzothiophenes [J].
Cho, YH ;
Kina, A ;
Shimada, T ;
Hayashi, T .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (11) :3811-3823
[5]   Chiral [2.2.2] dienes as ligands for Rh(I) in conjugate additions of boronic acids to a wide range of acceptors [J].
Defieber, C ;
Paquin, JF ;
Serna, S ;
Carreira, EM .
ORGANIC LETTERS, 2004, 6 (21) :3873-3876
[6]   The activation barrier to axial torsion in 2,2'-bis(diphenylphosphino)biphenyl [J].
Desponds, O ;
Schlosser, M .
TETRAHEDRON LETTERS, 1996, 37 (01) :47-48
[7]   Chiral poisoning and asymmetric activation [J].
Faller, JW ;
Lavoie, AR ;
Parr, J .
CHEMICAL REVIEWS, 2003, 103 (08) :3345-3367
[8]   CHIRAL POISONING IN THE KINETIC RESOLUTION OF ALLYLIC ALCOHOLS [J].
FALLER, JW ;
TOKUNAGA, M .
TETRAHEDRON LETTERS, 1993, 34 (46) :7359-7362
[9]   CHIRAL POISONING - A NOVEL STRATEGY FOR ASYMMETRIC CATALYSIS [J].
FALLER, JW ;
PARR, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (02) :804-805
[10]   CONTROLLING STEREOCHEMISTRY IN C-C AND C-H BOND FORMATION WITH ELECTRONICALLY ASYMMETRIC ORGANOMETALLICS AND CHIRAL POISONS [J].
FALLER, JW ;
MAZZIERI, MR ;
NGUYEN, JT ;
PARR, J ;
TOKUNAGA, M .
PURE AND APPLIED CHEMISTRY, 1994, 66 (07) :1463-1469