Dynamic Kinetic Resolution of α-Keto Esters via Asymmetric Transfer Hydrogenation

被引:121
作者
Steward, Kimberly M. [1 ]
Gentry, Emily C. [1 ]
Johnson, Jeffrey S. [1 ]
机构
[1] Univ N Carolina Chapel Hill, Dept Chem, Chapel Hill, NC 27515 USA
关键词
INTERMOLECULAR STETTER REACTION; ENANTIOSELECTIVE SYNTHESIS; M-TERPHENYLS; KETOAMIDES; COMPLEXES; ALDEHYDES;
D O I
10.1021/ja3027136
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The dynamic kinetic resolution of beta-aryl alpha-keto esters has been accomplished using a newly designed (arene)RuCl(monosulfonamide) transfer hydrogenation catalyst This dynamic process generates three contiguous stereocenters with remarkable diastereoselectivity through a reduction/lactonization sequence. The resulting enantioenriched, densely functionalized gamma-butyrolactones are of high synthetic utility, as highlighted by several secondary derivatizations.
引用
收藏
页码:7329 / 7332
页数:4
相关论文
共 28 条
[1]   An Organocatalytic Asymmetric Nazarov Cyclization [J].
Basak, Ashok K. ;
Shimada, Naoyuki ;
Bow, William F. ;
Vicic, David A. ;
Tius, Marcus A. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (24) :8266-+
[2]  
Bukowsa M., 1990, Pol. J. Chem, V64, P573
[3]   Chiral phosphoramide-catalyzed aldol additions of ketone trichlorosilyl enolates. Mechanistic aspects [J].
Denmark, SE ;
Pham, SM ;
Stavenger, RA ;
Su, XP ;
Wong, KT ;
Nishigaichi, Y .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (10) :3904-3922
[4]   Synthesis of phosphoramides for the Lewis base-catalyzed allylation and aldol addition reactions [J].
Denmark, SE ;
Su, YP ;
Nishigaichi, Y ;
Coe, DM ;
Wong, KT ;
Winter, SBD ;
Choi, JY .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (06) :1958-1967
[5]   Enantioselective synthesis of cis-α-substituted cycloalkanols and trans-cycloalkyl amines thereof [J].
Fernandez, Rosario ;
Ros, Abel ;
Magriz, Antonio ;
Dietrich, Hansjoerg ;
Lassaletta, Jose M. .
TETRAHEDRON, 2007, 63 (29) :6755-6763
[6]   Asymmetric catalytic hydrogenation. Design of new Ru catalysts and chiral ligands: From laboratory to industrial applications [J].
Genet, JP .
ACCOUNTS OF CHEMICAL RESEARCH, 2003, 36 (12) :908-918
[7]   ASYMMETRIC TRANSFER HYDROGENATION OF AROMATIC KETONES CATALYZED BY CHIRAL RUTHENIUM(II) COMPLEXES [J].
HASHIGUCHI, S ;
FUJII, A ;
TAKEHARA, J ;
IKARIYA, T ;
NOYORI, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (28) :7562-7563
[8]   Asymmetric transfer hydrogenation of ketones with bifunctional transition metal-based molecular [J].
Ikariya, Takao ;
Blacker, A. John .
ACCOUNTS OF CHEMICAL RESEARCH, 2007, 40 (12) :1300-1308
[9]   Stereospecific synthesis of C2 symmetric diamines from the mother diamine by resonance-assisted hydrogen-bond directed diaza-Cope rearrangement [J].
Kim, Hyunwoo ;
Nguyen, Yen ;
Yen, Cindy Pai-Hui ;
Chagal, Leonid ;
Lough, Alan J. ;
Kim, B. Moon ;
Chin, Jik .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (36) :12184-12191
[10]   The Renaissance of α-Methylene-γ-butyrolactones: New Synthetic Approaches [J].
Kitson, Russell R. A. ;
Millemaggi, Alessia ;
Taylor, Richard J. K. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (50) :9426-9451