A cobalt(III)-salen complex with an axial substituent in the diamine backbone: Stereoselective recognition of amino alcohols

被引：101
作者：
Kim, HJ
Kim, W
Lough, AJ
Kim, BM
Chin, J
机构：
[1] Univ Toronto, Dept Chem, Toronto, ON M5S 3H6, Canada
[2] Seoul Natl Univ, Sch Chem, Seoul 151747, South Korea
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2005年 / 127卷 / 48期
关键词：
D O I：
10.1021/ja0557785
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A cobalt(III)-salen complex (3) with an axial substituent on the diamine backbone has been synthesized. Crystal structure reveals that the axial substituent (p-nitrophenyl group) is positioned in close proximity to the metal binding site. The stereoselectivity of the cobalt complex for binding amino alcohols increases with increasing steric bulk of the amino alcohol from alaninol (2.9) to valinol (6.2) and t-leucinol (36.0). Copyright © 2005 American Chemical Society.
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页码：16776 / 16777
页数：2
相关论文
共 22 条
[1]   Stereoselective recognition of an aziridine with a Co(III) complex: A potential transition-state analogue for catalytic epoxidation [J].
Bobb, R ;
Alhakimi, G ;
Studnicki, L ;
Lough, A ;
Chin, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (17) :4544-4545
[2]   Controlling diaza-cope rearrangement reactions with resonance-assisted hydrogen bonds [J].
Chin, J ;
Mancin, F ;
Thavarajah, N ;
Lee, DY ;
Lough, A ;
Chung, DS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (50) :15276-15277
[3]   A metal complex that binds α-amino acids with high and predictable stereospecificity [J].
Chin, J ;
Lee, SS ;
Lee, KJ ;
Park, S ;
Kim, DH .
NATURE, 1999, 401 (6750) :254-257
[4]   Salen-derived catalysts containing secondary basic groups in the addition of diethylzinc to aldehydes [J].
DiMauro, EF ;
Kozlowski, MC .
ORGANIC LETTERS, 2001, 3 (19) :3053-3056
[5]   Enantioselective alkylations of tributyltin enolates catalyzed by Cr(salen)Cl: Access to enantiomerically enriched all-carbon quaternary centers [J].
Doyle, AG ;
Jacobsen, EN .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (01) :62-63
[6]  
Evans DA, 2001, ANGEW CHEM INT EDIT, V40, P1884, DOI 10.1002/1521-3773(20010518)40:10<1884::AID-ANIE1884>3.0.CO
[7]  
2-9
[8]   Evidence for intramolecular N-H•••O resonance-assisted hydrogen bonding in β-enaminones and related heterodienes.: A combined crystal-structural, IR and NMR spectroscopic, and quantum-mechanical investigation [J].
Gilli, P ;
Bertolasi, V ;
Ferretti, V ;
Gilli, G .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (42) :10405-10417
[9]   Asymmetric catalysis of epoxide ring opening reactions [J].
Jacobsen, EN .
ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (06) :421-431
[10]   CATALYTIC ASYMMETRIC OXIDATIONS USING OPTICALLY-ACTIVE (SALEN)MANGANESE(III) COMPLEXES AS CATALYSTS [J].
KATSUKI, T .
COORDINATION CHEMISTRY REVIEWS, 1995, 140 :189-214
123