Conceptually new chiral tertiary C2 symmetric diamines in asymmetric synthesis

被引:51
作者
Kizirian, JC
Caille, JC
Alexakis, A
机构
[1] Univ Geneva, Dept Organ Chem, CH-1211 Geneva 4, Switzerland
[2] PPG SIPSY, F-49242 Avrille, France
关键词
asymmetric synthesis; diamines; organolithiums; imines; C-2; symmetry;
D O I
10.1016/j.tetlet.2003.09.171
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
New chiral diamines were prepared, based on the cyclohexane diamine core. The two different substituents on each nitrogen allow this heteroatom to become a stereogenic center upon chelation with a metal, such as lithium. The enantioselective addition of MeLi to imines. with ee's up to 68%, illustrates the validity of this concept. (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码:8893 / 8895
页数:3
相关论文
共 32 条
[1]   A practical and efficient synthesis of chiral N,N-disubstituted C2 symmetric diamines derived from (R,R)-1,2-diaminocyclohexane [J].
Alexakis, A ;
Chauvin, AS ;
Stouvenel, R ;
Vrancken, E ;
Mutti, S ;
Mangeney, P .
TETRAHEDRON-ASYMMETRY, 2001, 12 (08) :1171-1178
[2]   A NEW REAGENT FOR THE DETERMINATION OF THE OPTICAL PURITY OF PRIMARY, SECONDARY, AND TERTIARY CHIRAL ALCOHOLS AND OF THIOLS [J].
ALEXAKIS, A ;
MUTTI, S ;
MANGENEY, P .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (04) :1224-1237
[3]   Enantioselective addition of organolithium reagents to imines mediated by C2-symmetric bis(aziridine) ligands [J].
Andersson, PG ;
Johansson, F ;
Tanner, D .
TETRAHEDRON, 1998, 54 (38) :11549-11566
[4]   Synthesis of enantiomerically enriched amines by chiral ligand mediated addition of organolithium reagents to imines [J].
Arrasate, S ;
Lete, E ;
Sotomayor, N .
TETRAHEDRON-ASYMMETRY, 2001, 12 (14) :2077-2082
[5]   Regioselective, diastereoselective, and enantioselective lithiation-substitution sequences: Reaction pathways and synthetic applications [J].
Beak, P ;
Basu, A ;
Gallagher, DJ ;
Park, YS ;
Thayumanavan, S .
ACCOUNTS OF CHEMICAL RESEARCH, 1996, 29 (11) :552-560
[6]   ENANTIOSELECTIVE SYNTHESIS OF SECONDARY ALCOHOLS IN THE PRESENCE OF CHIRAL LIGANDS [J].
COLOMBO, L ;
GENNARI, C ;
POLI, G ;
SCOLASTICO, C .
TETRAHEDRON, 1982, 38 (17) :2725-2727
[7]   ASYMMETRIC ADDITION OF ORGANOLITHIUM REAGENTS TO IMINES [J].
DENMARK, SE ;
NAKAJIMA, N ;
NICAISE, OJC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (19) :8797-8798
[8]   Effect of ligand structure in the bisoxazoline mediated asymmetric addition of methyllithium to imines [J].
Denmark, SE ;
Stiff, CM .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (18) :5875-5878
[9]  
FALORNI M, 1991, TETRAHEDRON-ASYMMETR, V4, P287
[10]   ASYMMETRIC CIS-DIHYDROXYLATION OF OLEFINS BY UTILIZING CHIRAL BISPIPERAZINE [J].
FUJI, K ;
TANAKA, K ;
MIYAMOTO, H .
TETRAHEDRON LETTERS, 1992, 33 (28) :4021-4024