SN2 vs. E2 on quaternary centres:: an application to the synthesis of enantiopure β2,2-amino acids

被引:47
作者
Avenoza, A [1 ]
Busto, JH [1 ]
Corzana, F [1 ]
Jiménez-Osés, G [1 ]
Peregrina, JM [1 ]
机构
[1] Univ La Rioja, Dept Quim, Grp Sintesis Quim Rioja, CSIC,UA, E-26006 Logrono, Spain
关键词
D O I
10.1039/b400282b
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
S(N)2 and E2 competing reactions in cyclic sulfamidates can be modulated by the change of an amide group to an ester group attached to the quaternary carbon activated for the nucleophilic attack, allowing an easy approach to enantiopure alpha,alpha-disubstituted beta-amino acids.
引用
收藏
页码:980 / 981
页数:2
相关论文
共 23 条
[1]   SYNTHESIS AND REACTIONS OF N-SULFONYLAMINES [J].
ATKINS, GM ;
BURGESS, EM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (17) :6135-&
[2]   New syntheses of enantiopure 2-methyl isoserines [J].
Avenoza, A ;
Busto, JH ;
Corzana, F ;
Jiménez-Osés, G ;
París, M ;
Peregrina, JM ;
Sucunza, D ;
Zurbano, MM .
TETRAHEDRON-ASYMMETRY, 2004, 15 (01) :131-137
[3]   Understanding the unusual regioselectivity in the nucleophilic ring-opening reactions of gem-disubstituted cyclic sulfates.: Experimental and theoretical studies [J].
Avenoza, A ;
Busto, JH ;
Corzana, F ;
García, JI ;
Peregrina, JM .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (11) :4506-4513
[4]   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
[5]   A NEW MIXING OF HARTREE-FOCK AND LOCAL DENSITY-FUNCTIONAL THEORIES [J].
BECKE, AD .
JOURNAL OF CHEMICAL PHYSICS, 1993, 98 (02) :1372-1377
[6]   β-peptides:: From structure to function [J].
Cheng, RP ;
Gellman, SH ;
DeGrado, WF .
CHEMICAL REVIEWS, 2001, 101 (10) :3219-3232
[7]   ASYMMETRIC-SYNTHESIS OF ALPHA-ALKYL-ALPHA-AMINO ACIDS FROM CHROMIUM CARBENE-COMPLEX-DERIVED BETA-LACTAMS [J].
COLSON, PJ ;
HEGEDUS, LS .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (22) :5918-5924
[8]  
Gademann K, 1999, ANGEW CHEM INT EDIT, V38, P1223, DOI 10.1002/(SICI)1521-3773(19990503)38:9<1223::AID-ANIE1223>3.0.CO
[9]  
2-A
[10]  
*GAUSS INC, 2001, GAUSS 98 REV A 11