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Asymmetric synthesis of α-amino carbonyl derivatives using lithium (R)-N-benzyl-N-α-methylbenzylamide

被引：21
作者：
Davies, SG
Epstein, SW
Garner, AC
Ichihara, O
Smith, AD
机构：
[1] Univ Oxford, Dyson Perrins Lab, Oxford OX1 3QY, England
[2] Evotec OAI, Abingdon OX14 4SD, Oxon, England
来源：
TETRAHEDRON-ASYMMETRY | 2002年 / 13卷 / 14期
基金：
英国工程与自然科学研究理事会;
关键词：
D O I：
10.1016/S0957-4166(02)00406-8
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
An efficient protocol for the transformation of homochiral alpha-hydroxy-beta-amino esters to their alpha-amino carbonyl components is presented. Diastereoselective conjugate addition of lithium (R)-N-benzyl-N-alpha-methylbenzylamide to a range of alpha,beta-unsaturated esters and subsequent enolate hydroxylation with (1R)-(-)-(camphorsulfonyl)oxaziridine, followed by LiAlH4 reduction produces homochiral 3-amino-1,2-diols. Subsequent oxidative cleavage with H5IO6 provides N-benzyl-N-alpha-methylbenzyl protected alpha-amino aldehydes (96-98% d.e.) and ketones (88% d.e.). Further oxidation of the alpha-amino aldehydes with sodium chlorite and Pd-catalysed hydrogenation provides alpha-amino acids in 94-98% e.e. (C) 2002 Elsevier Science Ltd. All rights reserved.
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收藏
页码：1555 / 1565
页数：11
相关论文
共 48 条
[1]  
ALBERTSON NF, 1946, J AM CHEM SOC, V68, P452
[2]  
BEAGLEY B, 1989, J CHEM SOC P1, V6, P1127
[3]   OXIDATION OF TERTIARY POLYCYCLIC AMINES BY RUO4 [J].
BETTONI, G ;
CARBONARA, G ;
FRANCHINI, C ;
TORTORELLA, V .
TETRAHEDRON, 1981, 37 (24) :4159-4164
[4]   A cobalt catalyzed protocol for the synthesis of substituted beta-phenyl isoserine derivatives [J].
Bhatia, B ;
Jain, S ;
De, A ;
Bagchi, I ;
Iqbal, J .
TETRAHEDRON LETTERS, 1996, 37 (40) :7311-7314
[5]   Asymmetric synthesis of N-protected syn and anti (E)-3-amino-2-hydroxy-4-hexenoate:: A practical method for the C-α epimerization of anti β-amino-α-hydroxy acids [J].
Brackenridge, I ;
Davies, SG ;
Fenwick, DR ;
Ichihara, O ;
Polywka, MEC .
TETRAHEDRON, 1999, 55 (02) :533-540
[6]   Orthogonal N,N-deprotection strategies of β-amino esters [J].
Bull, SD ;
Davies, SG ;
Kelly, PM ;
Gianotti, M ;
Smith, AD .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (23) :3106-3111
[7]   ASYMMETRIC-SYNTHESIS OF BETA-AMINO-ALPHA-HYDROXY ACIDS VIA DIASTEREOSELECTIVE HYDROXYLATION OF HOMOCHIRAL BETA-AMINO ENOLATES [J].
BUNNAGE, ME ;
CHERNEGA, AN ;
DAVIES, SG ;
GOODWIN, CJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (17) :2373-2384
[8]   ASYMMETRIC-SYNTHESIS OF THE TAXOL AND TAXOTERE C-13 SIDE-CHAINS [J].
BUNNAGE, ME ;
DAVIES, SG ;
GOODWIN, CJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (17) :2385-2391
[9]   ASYMMETRIC-SYNTHESIS OF THE N-TERMINAL COMPONENT OF MICROGININ - (2S,3R)-3-AMINO-2-HYDROXYDECANOIC ACID, ITS (2R,3R)-EPIMER AND (3R)-3-AMINODECANOIC ACID [J].
BUNNAGE, ME ;
BURKE, AJ ;
DAVIES, SG ;
GOODWIN, CJ .
TETRAHEDRON-ASYMMETRY, 1995, 6 (01) :165-176
[10]   (R)- and (S)-3-hydroxy-4,4-dimethyl-1-phenyl-2-pyrrolidinone as chiral auxiliaries in the enantioselective preparation of α-amino acids [J].
Camps, P ;
Pérez, F ;
Soldevilla, N ;
Borrego, MA .
TETRAHEDRON-ASYMMETRY, 1999, 10 (03) :493-509
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