Efficient hydrolysis of β-aminosulfamic acids using a Lewis acid and a thiol for the synthesis of 2,3-diaminopropanoate derivatives

被引:30
作者
Kim, BM [1 ]
So, SM
机构
[1] Seoul Natl Univ, Dept Chem, Seoul 151742, South Korea
[2] Seoul Natl Univ, Ctr Mol Catalysis, Seoul 151742, South Korea
关键词
amino acids and derivatives; sulfamic acid and derivatives; hydrolysis;
D O I
10.1016/S0040-4039(98)01079-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
New hydrolysis conditions for beta-aminosulfamic acids produced from the opening of a cyclic sulfamidate with a variety of primary or secondary amines have been developed. This new hydrolysis method allowed us to use at most two equivalents of amine nucleophiles furnishing 2,3-diaminopropanoate derivatives in good to excellent yields. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:5381 / 5384
页数:4
相关论文
共 26 条
[1]   Use of cyclic sulfamidates derived from D-allosamine in nucleophilic displacements: Scope and limitations [J].
Aguilera, B ;
FernandezMayoralas, A ;
Jaramillo, C .
TETRAHEDRON, 1997, 53 (16) :5863-5876
[2]   THE DIRECT SYNTHESIS OF THE CYCLIC SULPHAMIDATE OF (S)-PROLINOL - SIMULTANEOUS N-PROTECTION AND ACTIVATION TOWARDS NUCLEOPHILIC DISPLACEMENT OF OXYGEN [J].
ALKER, D ;
DOYLE, KJ ;
HARWOOD, LM ;
MCGREGOR, A .
TETRAHEDRON-ASYMMETRY, 1990, 1 (12) :877-880
[3]   CYCLIC SULPHAMIDATES - NEW SYNTHETIC PRECURSORS FOR BETA-FUNCTIONALIZED ALPHA-AMINO-ACIDS [J].
BALDWIN, JE ;
SPIVEY, AC ;
SCHOFIELD, CJ .
TETRAHEDRON-ASYMMETRY, 1990, 1 (12) :881-884
[4]  
BALDWIN JE, 1994, TETRAHEDRON, V50, P5049
[5]   SULFAMIC ACID AND ITS N-SUBSTITUTED DERIVATIVES [J].
BENSON, GA ;
SPILLANE, WJ .
CHEMICAL REVIEWS, 1980, 80 (02) :151-186
[6]  
Boehme RE, 1995, ANNU REP MED CHEM, V30, P139
[7]  
COLE DC, 1994, TETRAHEDRON, V50, P9517
[8]   ALKYLATION OF THE CYCLIC SULFAMATE OF PROLINOL - PREPARATION OF OPTICALLY-ACTIVE 2-ALKYL-SUBSTITUTED PYRROLIDINES [J].
COOPER, GF ;
MCCARTHY, KE ;
MARTIN, MG .
TETRAHEDRON LETTERS, 1992, 33 (40) :5895-5896
[9]  
COPPOLA GM, ASYMMETRIC SYNTHESIS, P87
[10]   RECENT DEVELOPMENTS IN THE STEREOSELECTIVE SYNTHESIS OF ALPHA-AMINO-ACIDS [J].
DUTHALER, RO .
TETRAHEDRON, 1994, 50 (06) :1539-1650