α-Alkylation versus retro-O-Michael/γ-alkylation of bicyclic N,O-acetals: an entry to α-methylthreonine

被引：7
作者：
Aydillo, Carlos [1 ]
Avenoza, Alberto [1 ]
Busto, Jesus H. [1 ]
Jimenez-Oses, Gonzalo [2 ]
Peregrina, Jesus M. [1 ]
Zurbano, Maria M. [1 ]
机构：
[1] Univ La Rioja, Dept Quim, Grp Sintesis Quim La Rioja, UA CSIC, E-26006 Logrono, Spain
[2] Univ Zaragoza, CSIC, Dept Quim Organ, E-50009 Zaragoza, Spain
来源：
TETRAHEDRON-ASYMMETRY | 2008年 / 19卷 / 24期
关键词：
D O I：
10.1016/j.tetasy.2008.11.031
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
The synthesis of a new threonine equivalent based on a bicyclic N,O-acetal substructure incorporating four stereogenic centres is developed from Boc-L-threonine methyl ester in one step. Its use as an excellent chiral building block was demonstrated in a new diastereoselective synthesis of alpha-methylthreonine by an alpha-alkylation reaction and in the synthesis of chiral alpha,beta-dehydroamino acid derivatives, using the tandem retro-O-Michael/gamma-alkylation reactions as key steps. (C) 2008 Elsevier Ltd. All rights reserved.
引用
收藏
页码：2829 / 2834
页数：6
相关论文
共 78 条
[1]  
Ager DJ, 2002, CURR OPIN DRUG DISC, V5, P892
[2]   Chemical diversity in the sialic acids and related α-keto acids:: An evolutionary perspective [J].
Angata, T ;
Varki, A .
CHEMICAL REVIEWS, 2002, 102 (02) :439-469
[3]  
[Anonymous], 1992, ALDRICHIM ACTA
[4]  
ARNOLD Z, 1990, SYNTHESIS-STUTTGART, P39
[5]  
ASHRY EL, 2005, LETT ORG CHEM, V2, P415
[6]   Alkylation of lithium dienediolates of butenoic acids. Regioselectivity effects of structure and leaving group of the alkylating agent. [J].
Aurell, MJ ;
Gil, S ;
Mestres, R ;
Parra, M ;
Parra, L .
TETRAHEDRON, 1998, 54 (17) :4357-4366
[7]   Diastereoselective synthesis of (S)- and (R)-α-phenylserine by a sulfinimine-mediated Strecker reaction [J].
Avenoza, A ;
Busto, JH ;
Corzana, F ;
Peregrina, JM ;
Sucunza, D ;
Zurbano, MM .
SYNTHESIS-STUTTGART, 2005, (04) :575-578
[8]   α-Methylserinals as an access to α-methyl-β-hydroxyamino acids:: application in the synthesis of all stereoisomers of α-methylthreonine [J].
Avenoza, A ;
Busto, JH ;
Corzana, F ;
Peregrina, JM ;
Sucunza, D ;
Zurbano, MM .
TETRAHEDRON-ASYMMETRY, 2004, 15 (04) :719-724
[9]   Synthesis of enantiopure (αMe)Dip and other α-methylated β-branched amino acid derivatives [J].
Avenoza, A ;
Busto, JH ;
Cativiela, C ;
Peregrina, JM ;
Sucunza, D ;
Zurbano, MM .
TETRAHEDRON-ASYMMETRY, 2003, 14 (03) :399-405
[10]   Enantioselective synthesis of (S)- and (R)-α-methylserines:: application to the synthesis of (S)- and (R)-N-Boc-N,O-isopropylidene-α-methylserinals [J].
Avenoza, A ;
Cativiela, C ;
Corzana, F ;
Peregrina, JM ;
Sucunza, D ;
Zurbano, MM .
TETRAHEDRON-ASYMMETRY, 2001, 12 (06) :949-957
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