Catalytic enantioselective aldol additions of α-isothiocyanato imides to aldehydes

被引:88
作者
Li, Le [1 ]
Klauber, Eric G. [1 ]
Seidel, Daniel [1 ]
机构
[1] Rutgers State Univ, Dept Chem & Chem Biol, Piscataway, NJ 08854 USA
关键词
D O I
10.1021/ja804838y
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Highly enantioselective organocatalytic aldol additions of aisothiocyanato imides to aldehydes are reported. These reactions provide convenient access to enantiomerically enriched and protected beta-hydroxy-a-amino acids with catalyst loadings as low as 1 mol%.
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页码:12248 / +
页数:3
相关论文
共 57 条
[1]   TOTAL SYNTHESIS OF BOUVARDIN, O-METHYLBOUVARDIN, AND O-METHYL-N-9-DESMETHYLBOUVARDIN [J].
BOGER, DL ;
PATANE, MA ;
ZHOU, JC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (19) :8544-8556
[2]   TOTAL SYNTHESIS OF BLEOMYCIN-A(2) AND RELATED AGENTS .1. SYNTHESIS AND DNA-BINDING PROPERTIES OF THE EXTENDED C-TERMINUS - TRIPEPTIDE-S, TETRAPEPTIDE-S, PENTAPEPTIDE-S, AND RELATED AGENTS [J].
BOGER, DL ;
COLLETTI, SL ;
HONDA, T ;
MENEZES, RF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (13) :5607-5618
[3]   Preparation of α-amino-carboxylic acid derivatives via diastereoselective reactions of glycine enolate equivalents [J].
Caddick, S ;
Parr, NJ ;
Pritchard, MC .
TETRAHEDRON, 2001, 57 (30) :6615-6626
[4]   Organocatalysis mediated by (thio)urea derivatives [J].
Connon, Stephen J. .
CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (21) :5418-5427
[5]   Expedient synthesis of threo-β-hydroxy-α-amino acid derivatives:: Phenylalanine, tyrosine, histidine, and tryptophan [J].
Crich, David ;
Banerjee, Abhisek .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (18) :7106-7109
[6]   Total synthesis of the ristocetin aglycon [J].
Crowley, BM ;
Mori, Y ;
McComas, CC ;
Tang, DT ;
Boger, DL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (13) :4310-4317
[7]   Total synthesis of exochelin MN and analogues [J].
Dong, L ;
Miller, MJ .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (14) :4759-4770
[8]   Small-molecule H-bond donors in asymmetric catalysis [J].
Doyle, Abigail G. ;
Jacobsen, Eric N. .
CHEMICAL REVIEWS, 2007, 107 (12) :5713-5743
[9]  
Evans DA, 2001, ANGEW CHEM INT EDIT, V40, P1884, DOI 10.1002/1521-3773(20010518)40:10<1884::AID-ANIE1884>3.0.CO
[10]  
2-9