Enantiopure β-hydroxy morpholine amides from terminal epoxides by carbonylation at 1 atm

被引:46
作者
Goodman, SN [1 ]
Jacobsen, EN [1 ]
机构
[1] Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
关键词
amides; carbonylation; cobalt; epoxides; homogeneous catalysis;
D O I
10.1002/anie.200290022
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Keeping the CO pressure down is a crucial, practical feature of the new methodology for the carbonylation of terminal epoxides. β-Hydroxy morpholinyl amides are generated directly in optically pure form [Eq. (1)], and these building blocks can be applied in a variety of acyl transfer reactions. A useful illustration is provided in the concise synthesis of δ-hydroxy-β-ketoesters, key intermediates for the preparation of the statin class of HMG-CoA reductase inhibitors.
引用
收藏
页码:4703 / 4705
页数:3
相关论文
共 26 条
[11]  
Mahadevan V, 2002, ANGEW CHEM INT EDIT, V41, P2781, DOI 10.1002/1521-3773(20020802)41:15<2781::AID-ANIE2781>3.0.CO
[12]  
2-S
[13]  
Mahadevan V., 2002, ANGEW CHEM, V114, P2905
[14]  
Martin R, 1997, SYNLETT, P1414
[15]  
McFarlane IM, 1999, PROCESS CHEMISTRY IN THE PHARMACEUTICAL INDUSTRY, P243
[16]   OXYMETHYLATIVE OPENING OF OXIRANES LEADING TO 1,3-DIOL DERIVATIVES BY COBALT CARBONYL CATALYZED REACTION WITH A HYDROSILANE AND CARBON-MONOXIDE [J].
MURAI, T ;
KATO, S ;
MURAI, S ;
TOKI, T ;
SUZUKI, S ;
SONODA, N .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (20) :6093-6095
[17]   COBALT CARBONYL CATALYZED-REACTIONS OF CYCLIC ETHERS WITH A HYDROSILANE AND CARBON-MONOXIDE - A NEW SYNTHETIC REACTION EQUIVALENT TO NUCLEOPHILIC OXYMETHYLATION [J].
MURAI, T ;
YASUI, E ;
KATO, S ;
HATAYAMA, Y ;
SUZUKI, S ;
YAMASAKI, Y ;
SONODA, N ;
KUROSAWA, H ;
KAWASAKI, Y ;
MURAI, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (20) :7938-7946
[18]   THE SYNTHESIS OF MEVINIC ACIDS [J].
ROSEN, T ;
HEATHCOCK, CH .
TETRAHEDRON, 1986, 42 (18) :4909-4951
[19]   Highly selective hydrolytic kinetic resolution of terminal epoxides catalyzed by chiral (salen)CoIII complexes.: Practical synthesis of enantioenriched terminal epoxides and 1,2-diols [J].
Schaus, SE ;
Brandes, BD ;
Larrow, JF ;
Tokunaga, M ;
Hansen, KB ;
Gould, AE ;
Furrow, ME ;
Jacobsen, EN .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (07) :1307-1315
[20]   Amino acid derived morpholine amides for nucleophilic α-amino acylation reactions:: A new synthetic route to enantiopure α-amino ketones [J].
Sengupta, S ;
Mondal, S ;
Das, D .
TETRAHEDRON LETTERS, 1999, 40 (21) :4107-4110