A CONVENIENT SYNTHESIS OF CHIRAL OXAZOLIDIN-2-ONES AND THIAZOLIDIN-2-ONES AND AN IMPROVED PREPARATION OF TRIPHOSGENE

被引：31
作者：
FALB, E [1 ]
NUDELMAN, A [1 ]
HASSNER, A [1 ]
机构：
[1] BAR ILAN UNIV,DEPT CHEM,IL-52900 RAMAT GAN,ISRAEL
来源：
SYNTHETIC COMMUNICATIONS | 1993年 / 23卷 / 20期
关键词：
D O I：
10.1080/00397919308012605
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Oxazolidin-2-ones and thiazolidin-2-one are conveniently prepared by condensation of L-serine, L-threonine and L-cysteine, respectively with triphosgene. The corresponding methyl esters may be subsequently obtained by quenching the reaction mixture with methanol, without prior need for the isolation of the free acids. An improved procedure for preparation of triphosgene using an internal cooling system is described.
引用
收藏
页码：2839 / 2844
页数：6
相关论文
共 50 条
[21]   A SIMPLE ROUTE TO ENANTIOMERICALLY ENRICHED OXAZOLIDIN-2-ONES [J].
XU, DQ ;
SHARPLESS, KB .
TETRAHEDRON LETTERS, 1993, 34 (06) :951-952
[22]   SYNTHESIS OF OXAZOLIDIN-2-ONES USING CARBONATE ION ON A POLYMERIC SUPPORT [J].
CARDILLO, G ;
ORENA, M ;
SANDRI, S ;
TOMASINI, C .
TETRAHEDRON, 1985, 41 (01) :163-167
[23]   Resolution of pentafluorophenyl esters using oxazolidin-2-ones [J].
Al Shaye, Najla ;
Eames, Jason .
TETRAHEDRON LETTERS, 2010, 51 (45) :5892-5895
[24]   Microwave-Assisted Improved Synthesis of Oxazolidin-2-ones, Oxazolidine-2-thiones and Thiazolidine-2-thione Chiral Auxiliaries [J].
Morales-Nava, Rosmarbel ;
Fernandez-Zertuche, Mario ;
Ordonez, Mario .
MOLECULES, 2011, 16 (10) :8803-8814
[25]   CYCLIZATIONS OF AZIDOFORMATES TO TETRAHYDRO-1,3-OXAZIN-2-ONES AND OXAZOLIDIN-2-ONES [J].
ALEWOOD, PF ;
BENN, M ;
REINFRIED, R .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1974, 52 (24) :4083-4089
[26]   D-xylose derived oxazolidin-2-ones as chiral auxiliaries in stereoselective alkylations [J].
Koll, P ;
Lutzen, A .
TETRAHEDRON-ASYMMETRY, 1996, 7 (03) :637-640
[27]   Electrogenerated base-induced N-acylation of chiral oxazolidin-2-ones [J].
Feroci, M ;
Inesi, A ;
Palombi, L ;
Rossi, L ;
Sotgiu, G .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (18) :6185-6188
[28]   Synthesis of chiral oxazolidin-2-ones from N-alkoxycarbonyl amino epoxides:: a computational study [J].
Casado-Bellver, FJ ;
González-Rosende, ME ;
Asensio, A ;
Jordá-Gregori, JM ;
Alvarez-Sorolla, A ;
Sepúlveda-Arques, J ;
Orena, M ;
Galeazzi, R .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (14) :1650-1654
[29]   Practical modifications and applications of the sharpless asymmetric aminohydroxylation in the one-pot preparation of chiral oxazolidin-2-ones [J].
Barta, NS ;
Sidler, DR ;
Somerville, KB ;
Weissman, SA ;
Larsen, RD ;
Reider, PJ .
ORGANIC LETTERS, 2000, 2 (18) :2821-2824
[30]   Solid phase synthesis of 3,5-disubstituted oxazolidin-2-ones [J].
Rastogi, SK ;
Srivastava, GK ;
Singh, SK ;
Grover, RK ;
Roy, R ;
Kundu, B .
TETRAHEDRON LETTERS, 2002, 43 (46) :8327-8330
12345