Highly stereoselective formation of Cp*IrCl complexes of N,N-dimethylamino acids

被引:40
作者
Grotjahn, DB [1 ]
Joubran, C [1 ]
Hubbard, JL [1 ]
机构
[1] UTAH STATE UNIV,DEPT CHEM & BIOCHEM,LOGAN,UT 84322
关键词
D O I
10.1021/om9507890
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
N,N-Dimethylamino acids serve as (N, O)-chelating monoanionic ligands to the prochiral fragment Cp*IrCl. A series of four such complexes and one Rh analog all were formed with diastereoselectivity of greater than or equal to 50: less than or equal to 1. The structure of the valine complex 5d (C17H29ClIrNO2) was analyzed at 298 K, from which a cis-arrangement of Cp* and valine side chain (i-Pr) was revealed. Solution NMR studies of 5d, aided by an unusual zero coupling between the two methine protons of the amino acid, showed that the structures in solution and the solid were very similar. The preference for the cis-oriented Cp* and amino acid side chain in 5 is attributed to a maximum number of gauche interactions in the metallacycle and its substituents, especially pronounced for N,N-disubstituted amino acids.
引用
收藏
页码:1230 / 1235
页数:6
相关论文
共 46 条
[1]  
ABRAHAM RJ, 1988, INTRO NMR SPECTROSCO, pCH3
[2]   METAL-COMPLEXES OF BIOLOGICALLY IMPORTANT LIGANDS .68. ORGANOMETALLIC ASPARAGINATO COBALT COMPLEXES AS LIGANDS FOR ALKALINE IONS [J].
BERGS, R ;
SUNKEL, K ;
BECK, W .
CHEMISCHE BERICHTE-RECUEIL, 1993, 126 (11) :2429-2432
[3]   N-SUBSTITUTED AMINO-ACIDS .1. A NEW METHOD OF PREPARATION OF DIMETHYLAMINO-ACIDS [J].
BOWMAN, RE ;
STROUD, HH .
JOURNAL OF THE CHEMICAL SOCIETY, 1950, (MAY) :1342-1345
[4]  
BRUNNER H, 1988, TOP STEREOCHEM, V18, P129
[5]   MONOMERIC METAL-HYDROXIDES, ALKOXIDES, AND AMIDES OF THE LATE TRANSITION-METALS - SYNTHESIS, REACTIONS, AND THERMOCHEMISTRY [J].
BRYNDZA, HE ;
TAM, W .
CHEMICAL REVIEWS, 1988, 88 (07) :1163-1188
[6]   CHIRAL IRIDIUM(III) ALPHA-AMINO ACIDATO COMPLEXES (RIR,SN,SC)-[(ETA-5-C5ME5)IR(L-PROLINATE)(CC-CME3)] AND (SIR,SN,SC)-[(ETA-5-C5ME5)IR(L-PROLINATE)(CC-CME3)] [J].
CARMONA, D ;
LAHOZ, FJ ;
ATENCIO, R ;
ORO, LA ;
LAMATA, MP ;
JOSE, ES .
TETRAHEDRON-ASYMMETRY, 1993, 4 (07) :1425-1428
[7]   OPTICALLY-ACTIVE PSEUDOCTAHEDRAL RHODIUM(III), IRIDIUM(III), AND RUTHENIUM(II) COMPLEXES WITH ALPHA-AMINO ACIDATO LIGANDS - CRYSTAL-STRUCTURES OF RIRSCSN-[(C5ME5)IR(PRO)CL].1/2H2O AND SIRSCSN-[(C5ME5)IR(PRO)CL].1/2H2O (HPRO = L-PROLINE) [J].
CARMONA, D ;
MENDOZA, A ;
LAHOZ, FJ ;
ORO, LA ;
LAMATA, MP ;
JOSE, ES .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1990, 396 (01) :C17-C21
[8]   N-H ACTIVATION .1. OXIDATIVE ADDITION OF AMMONIA TO IRIDIUM(I) - ISOLATION, STRUCTURAL CHARACTERIZATION, AND REACTIVITY OF AMIDOIRIDIUM HYDRIDES [J].
CASALNUOVO, AL ;
CALABRESE, JC ;
MILSTEIN, D .
INORGANIC CHEMISTRY, 1987, 26 (07) :971-973
[9]   BIOORGANOMETALLIC CHEMISTRY .5. MOLECULAR RECOGNITION OF AROMATIC AMINO-ACID GUESTS BY CP-ASTERISK-RH-NUCLEOBASE/NUCLEOSIDE/NUCLEOTIDE CYCLIC TRIMER HOSTS IN AQUEOUS-SOLUTION [J].
CHEN, H ;
MAESTRE, MF ;
FISH, RH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (12) :3631-3632
[10]   AMINO-ACID DERIVATIVES OF TUNGSTEN CARBONYL - STRUCTURE AND REACTIVITY INVESTIGATIONS OF ZEROVALENT TUNGSTEN GLYCINE DERIVATIVES [J].
DARENSBOURG, DJ ;
ATNIP, EV ;
KLAUSMEYER, KK ;
REIBENSPIES, JN .
INORGANIC CHEMISTRY, 1994, 33 (23) :5230-5237