Highly diastereoselective synthesis of β-amino alcohols

被引:7
作者
Meester, WJN
van Dijk, R
van Maarseveen, JH
Rutjes, FPJT
Hermkens, PHH
Hiemstra, H
机构
[1] Univ Amsterdam, Inst Mol Chem, NL-1018 WS Amsterdam, Netherlands
[2] Univ Nijmegen, Dept Organ Chem, NL-6525 ED Nijmegen, Netherlands
[3] NV Organon, Lead Discovery Unit, NL-5340 BH Oss, Netherlands
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 2001年 / 22期
关键词
D O I
10.1039/b108254j
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Several substituted beta -amino alcohols 1 were synthesised in a diastereoselective manner via the novel highly versatile intermediate 8b, involving a combination of N-acyliminium ion and Weinreb amide chemistry.
引用
收藏
页码:2909 / 2911
页数:3
相关论文
共 12 条
[1]   The synthesis of vicinal amino alcohols [J].
Bergmeier, SC .
TETRAHEDRON, 2000, 56 (17) :2561-2576
[2]   Stereoselective synthesis of threo and erythroβ-hydroxy and β-disubstituted-β-hydroxy α-amino acids [J].
Blaskovich, MA ;
Evindar, G ;
Rose, NGW ;
Wilkinson, S ;
Luo, Y ;
Lajoie, GA .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (11) :3631-3646
[3]  
Fürstner A, 2000, ANGEW CHEM INT EDIT, V39, P3012
[4]   Auxiliary agents for the peroral administration of peptide and protein drugs:: Synthesis and evaluation of novel pepstatin analogues [J].
Kratzel, M ;
Hiessböck, R ;
Bernkop-Schnürch, A .
JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (13) :2339-2344
[5]   Synthesis of homoallylic amines via N-acyliminium ion reactions on solid support [J].
Meester, WJN ;
Rutjes, FPJT ;
Hermkens, PHH ;
Hiemstra, H .
TETRAHEDRON LETTERS, 1999, 40 (08) :1601-1604
[6]   SYNTHESIS OF GAMMA,DELTA-UNSATURATED ALPHA-AMINO-ACIDS FROM ALLYLSILANES AND GLYCIDYL CATION EQUIVALENTS [J].
MOOIWEER, HH ;
HIEMSTRA, H ;
SPECKAMP, WN .
TETRAHEDRON, 1989, 45 (14) :4627-4636
[7]   N-METHOXY-N-METHYLAMIDES AS EFFECTIVE ACYLATING AGENTS [J].
NAHM, S ;
WEINREB, SM .
TETRAHEDRON LETTERS, 1981, 22 (39) :3815-3818
[8]   SYNTHESIS OF RACEMIC ALPHA-AMINO CARBOXAMIDES VIA LEWIS ACID-MEDIATED REACTIONS OF ALPHA-METHOXYGLYCINAMIDE DERIVATIVES WITH ALLYLSILANES - ENZYMATIC RESOLUTION TO OPTICALLY-ACTIVE ALPHA-AMINO-ACIDS [J].
ROOS, EC ;
MOOIWEER, HH ;
HIEMSTRA, H ;
SPECKAMP, WN ;
KAPTEIN, B ;
BOESTEN, WHJ ;
KAMPHUIS, J .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (25) :6769-6778
[9]   New developments in the chemistry of N-acyliminium ions and related intermediates [J].
Speckamp, WN ;
Moolenaar, MJ .
TETRAHEDRON, 2000, 56 (24) :3817-3856
[10]   Development and application of allyl, 2-sulfonylethyl and 2-thioethyl carbamate linkers for solid phase N-acyliminium ion chemistry [J].
van Maarseveen, JH ;
Meester, WJN ;
Veerman, JJN ;
Kruse, CG ;
Hermkens, PHH ;
Rutjes, FPJT ;
Hiemstra, H .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (09) :994-1001