Enantiopure oxazolidinones as chiral acids in the asymmetric protonation of N-Boc pyrrole derived enolates

被引:17
作者
Carbery, DR [1 ]
Donohoe, TJ [1 ]
机构
[1] Univ Oxford, Dyson Perrins Lab, Oxford OX1 3QY, England
关键词
D O I
10.1039/b316719d
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The first use of geminally disubstituted oxazolidinones as chiral protonating agents is described: these new acids are able to directly protonate an enolate generated by the ammonia free partial reduction of an electron deficient pyrrole and give up to 68% ee in the pyrroline product.
引用
收藏
页码:722 / 723
页数:2
相关论文
共 14 条
[1]   4-SUBSTITUTED-5,5-DIMETHYL OXAZOLIDIN-2-ONES AS EFFECTIVE CHIRAL AUXILIARIES FOR ENOLATE ALKYLATIONS AND MICHAEL ADDITIONS [J].
DAVIES, SG ;
SANGANEE, HJ .
TETRAHEDRON-ASYMMETRY, 1995, 6 (03) :671-674
[2]   Diastereoselective reductive aldol reactions of Boc-protected electron deficient pyrroles [J].
Donohoe, TJ ;
House, D .
TETRAHEDRON LETTERS, 2003, 44 (05) :1095-1098
[3]   Scope of the reductive aldol reaction: application to aromatic carbocycles and heterocycles [J].
Donohoe, TJ ;
House, D ;
Ace, KW .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2003, 1 (21) :3749-3757
[4]   Ammonia free partial reduction of aromatic compounds using lithium di-tert-butylbiphenyl (LiDBB) [J].
Donohoe, TJ ;
House, D .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (14) :5015-5018
[5]  
DORMOY JR, 1982, SYNTHESIS-STUTTGART, P753
[6]   Recent advances into the enantioselective protonation of prostereogenic enol derivatives [J].
Eames, J ;
Weerasooriya, N .
TETRAHEDRON-ASYMMETRY, 2001, 12 (01) :1-24
[7]  
Fehr C, 1996, ANGEW CHEM INT EDIT, V35, P2567
[8]  
Hintermann T, 1998, HELV CHIM ACTA, V81, P2093, DOI 10.1002/(SICI)1522-2675(19981111)81:11<2093::AID-HLCA2093>3.0.CO
[9]  
2-X
[10]   Synthetic studies toward astins A, B and C.: Efficient syntheses of cis-3,4-dihydroxyprolines and (-)-(3S,4R)-dichloroproline esters [J].
Schumacher, KK ;
Jiang, JJ ;
Joullié, MM .
TETRAHEDRON-ASYMMETRY, 1998, 9 (01) :47-53