Parallel synthesis of homochiral β-amino acids

被引:45
作者
Davies, Stephen G. [1 ]
Mulvaney, Andrew W. [1 ]
Russell, Angela J. [1 ]
Smith, Andrew D. [1 ]
机构
[1] Univ Oxford, Chem Res Lab, Dept Organ Chem, Oxford OX1 3TA, England
基金
英国生物技术与生命科学研究理事会;
关键词
D O I
10.1016/j.tetasy.2007.06.008
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The parallel asymmetric synthesis of an array of 30 P-amino acids of high enantiomeric purity using the conjugate addition of homochiral lithium N-benzyl-N-(alpha-methylbenzyl)amide as the key step is accomplished. The experimental simplicity and highly practical nature of the protocol is demonstrated by the efficient parallel conversion of 15 alpha,beta-unsaturated esters to both enantiomeric series of the corresponding beta-amino acids in high overall yields and selectivities with minimal purification involved in each step of the reaction protocol. (C) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1554 / 1566
页数:13
相关论文
共 62 条
[51]   β2- and β3-peptides with proteinaceous side chains:: Synthesis and solution structures of constitutional isomers, a novel helical secondary structure and the influence of solvation and hydrophobic interactions on folding [J].
Seebach, D ;
Abele, S ;
Gademann, K ;
Guichard, G ;
Hintermann, T ;
Jaun, B ;
Matthews, JL ;
Schreiber, JV .
HELVETICA CHIMICA ACTA, 1998, 81 (05) :932-982
[52]   Enantioselective synthesis of α,β-disubstituted-β-amino acids [J].
Sibi, MP ;
Prabagaran, N ;
Ghorpade, SG ;
Jasperse, CP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (39) :11796-11797
[53]   BIOCATALYTIC APPROACH TO ENANTIOMERICALLY PURE BETA-AMINO ACIDS [J].
SOLOSHONOK, VA ;
FOKINA, NA ;
RYBAKOVA, AV ;
SHISHKINA, IP ;
GALUSHKO, SV ;
SOROCHINSKY, AE ;
KUKHAR, VP ;
SAVCHENKO, MV ;
SVEDAS, VK .
TETRAHEDRON-ASYMMETRY, 1995, 6 (07) :1601-1610
[54]  
Stavenger RA, 2001, ANGEW CHEM INT EDIT, V40, P3417, DOI 10.1002/1521-3773(20010917)40:18<3417::AID-ANIE3417>3.0.CO
[55]  
2-E
[56]  
Tamariz J., 1996, ENANTIOSELECTIVE SYN, P45
[57]   Asymmetric synthesis of β-amino acid derivatives incorporating a broad range of substitution patterns by enolate additions to tert-butanesulfinyl imines [J].
Tang, TP ;
Ellman, JA .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (22) :7819-7832
[58]   Synthesis of functionalized heterocycles via a tandem Staudinger/aza-Wittig/Ugi multicomponent reaction [J].
Timmer, MSM ;
Risseeuw, MDP ;
Verdoes, M ;
Filippov, DV ;
Plaisier, JR ;
van der Marel, GA ;
Overkleeft, HS ;
van Boom, JH .
TETRAHEDRON-ASYMMETRY, 2005, 16 (01) :177-185
[59]   Stereocontrolled solid-phase synthesis of fluorinated partially-modified retropeptides via tandem aza-Michael/enolate-protonation [J].
Volonterio, A ;
Chiva, G ;
Fustero, S ;
Piera, J ;
Rosello, MS ;
Sani, M ;
Zanda, M .
TETRAHEDRON LETTERS, 2003, 44 (37) :7019-7022
[60]   ASYMMETRIC SYNTHESIS OF (S)-HOMOPROLINE AND (S)-HOMOPIPECOLIC ACID [J].
WAKABAYASHI, T ;
WATANABE, K ;
KATO, Y .
SYNTHETIC COMMUNICATIONS, 1977, 7 (04) :239-244