A highly stereoselective synthesis of (2S,3S)-beta-hydroxyleucine

被引:28
作者
Laib, T [1 ]
Chastanet, J [1 ]
Zhu, JP [1 ]
机构
[1] CNRS,INST CHIM SUBST NAT,F-91198 GIF SUR YVETTE,FRANCE
关键词
ALPHA-AMINO-ACIDS; ASYMMETRIC-SYNTHESIS; ORGANIC-SYNTHESIS; (2S; 3S)-3-HYDROXYLEUCINE; (2R; 3R)-3-HYDROXYLEUCINE; CONVERSION; ALDEHYDES;
D O I
10.1016/S0040-4039(97)00207-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A highly diastereoselective nucleophilic addition of Grignard reagent to N,N-dibenzyl-O-TBS-serinal 3 was the key step in the present synthesis of(2S,3s)-beta-hydroxyleucine 1. (C) 1997 Published by Elsevier Science Ltd.
引用
收藏
页码:1771 / 1772
页数:2
相关论文
共 50 条
[41]   An Asymmetric Synthesis of (2S,5S)-5-Substituted Azepane-2-Carboxylate Derivatives [J].
Wishka, Donn G. ;
Bedard, Marion ;
Brighty, Katherine E. ;
Buzon, Richard A. ;
Farley, Kathleen A. ;
Fichtner, Michael W. ;
Kauffman, Goss S. ;
Kooistra, Jaap ;
Lewis, Jason G. ;
O'Dowd, Hardwin ;
Samardjiev, Ivan J. ;
Samas, Brian ;
Yalamanchi, Geeta ;
Noe, Mark C. .
JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (06) :1937-1940
[42]   A concise enantioselective synthesis of (2S,3S)-3-hydroxypipecolic acid via proline catalyzed α-aminooxylation of aldehydes and Pd-catalyzed ether directed aza-Claisen rearrangements [J].
Ahuja, Brij Bhushan ;
Sudalai, Arumugam .
TETRAHEDRON-ASYMMETRY, 2015, 26 (01) :24-28
[43]   A concise enantioselective synthesis of L-(-)-733,061 and (2S,3S)-methyl 3-aminopiperidine-2-carboxylate using catalytic enantioselective aza-Henry reaction as key step [J].
Kumaraswamy, Gullapalli ;
Pitchaiah, Arigala .
TETRAHEDRON, 2011, 67 (14) :2536-2541
[44]   Asymmetric synthesis of (2S,3S)- and (2R,3R)-α,β-dialkyl-α-amino acids via alkylation of chiral nickel(II) complexes of aliphatic α-amino acids with racemic α-alkylbenzyl bromides [J].
Soloshonok, Vadim A. ;
Boettiger, Thomas U. ;
Bolene, Shawna B. .
SYNTHESIS-STUTTGART, 2008, (16) :2594-2602
[45]   Asymmetric Synthesis of (-)-(1R,2S)-Myrislignan [J].
Xia Ya-Mu ;
Chang Liang .
CHEMICAL JOURNAL OF CHINESE UNIVERSITIES-CHINESE, 2010, 31 (09) :1780-1785
[46]   Improvements to Enable the Large Scale Synthesis of 1-{[(2S,3S,4S)-3-Ethyl-4-fluoro-5-oxopyrrolidin-2-yl]methoxy}-7-methoxyisoquinoline-6-carboxamide (PF-06650833) [J].
Wright, Stephen W. ;
Li, Bryan ;
Peng, Zhihui ;
Wei, Lulin ;
McInturff, Emma ;
Place, David ;
Damon, David B. ;
Singer, Robert A. .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2018, 22 (12) :1835-1845
[47]   A novel nonclassical Wittig reaction of dioxolanones:: highly facile and concise enantiospecific synthesis of (3S,4S)-3-hydroxy-4-phenylbutyrolactone [J].
Reddy, GV ;
Sreevani, V ;
Iyengar, DS .
TETRAHEDRON LETTERS, 2001, 42 (03) :531-532
[48]   Stereoselective Approach towards the Synthesis of 3R, 5 S Gingerdiol and 3 S, 5 S Gingerdiol [J].
Markad, Sachin B. ;
Bhosale, Viraj A. ;
Bokale, Suvarna R. ;
Waghmode, Suresh B. .
CHEMISTRYSELECT, 2019, 4 (02) :502-505
[49]   First enantioselective synthesis of (2S,3S)-3-hydroxy-L-arginine via proline catalyzed α-aminooxylation of aldehyde and Pd-catalyzed ether-directed aza-Claisen rearrangement [J].
Ahuja, Brij Bhushan ;
Sudalai, Arumugam .
TETRAHEDRON-ASYMMETRY, 2015, 26 (10-11) :548-552
[50]   A highly stereoselective synthesis of beta-trifluoromethylated homoallylic alcohols in water [J].
Loh, TP ;
Li, XR .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (09) :980-982