Trading N and O. Part 2: Exploiting aziridinium intermediates for the synthesis of β-hydroxy-α-amino acids

被引：18
|
作者：
Davies, Stephen G. [1 ]
Fletcher, Ai M. [1 ]
Frost, Aileen B. [1 ]
Roberts, Paul M. [1 ]
Thomson, James E. [1 ]
机构：
[1] Univ Oxford, Chem Res Lab, Dept Chem, Oxford OX1 3TA, England
来源：
TETRAHEDRON | 2014年 / 70卷 / 35期
关键词：
Asymmetric synthesis; Lithium amide; Aziridinium; beta-Hydroxy-alpha-amino acids; PARALLEL KINETIC RESOLUTION; HOMOCHIRAL LITHIUM AMIDES; DIASTEREOSELECTIVE CONJUGATE ADDITION; JASPINE-B PACHASTRISSAMINE; D-LYXO-PHYTOSPHINGOSINE; ASYMMETRIC-SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; AMMONIA EQUIVALENTS; ALDOL REACTIONS;
D O I：
10.1016/j.tet.2014.06.057
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The beta-hydroxy-alpha-amino acids (S,S)-allo-threonine, (S,S)-beta-hydroxyleucine and a range of aryl substituted (S,S)-beta-hydroxyphenylalanines were prepared from the corresponding enantiopure anti-alpha-hydroxy-beta amino esters via a rearrangement protocol, which proceeds via the intermediacy of the corresponding aziridinium ions. The starting anti-alpha-hydroxy-beta-amino esters were prepared in >99:1 dr using our diastereoselective aminohydroxylation procedure, whereby conjugate addition of lithium (R)-N-benzyl-N-(alpha-methylbenzyl)amide to an alpha,beta-unsaturated ester is followed by oxidation of the resultant enolate with (-)-camphorsulfonyloxaziridine. Subsequent activation of the hydroxyl group within the anti-alpha-hydroxy-beta-amino esters promoted aziridinium ion formation [which proceeds with inversion of configuration at C(2)], and regioselective ring-opening of the intermediate aziridinium ions with H2O [which proceeds with inversion of configuration at C(3)] gave the corresponding anti-beta-hydroxy-alpha-amino esters as single diastereoisomers (>99:1 dr). Deprotection of these substrates via sequential hydrogenolysis and ester hydrolysis gave the corresponding beta-hydroxy-alpha-amino acids in good yield and high diastereoisomeric and enantiomeric purity. (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码：5849 / 5862
页数：14
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