Synthesis of (2R,3S)-(-)-2-phenyl-3-methylaziridine

被引:20
作者
Galindo, A
Orea, FL
Gnecco, D
Enriquez, RG
Toscano, RA
Reynolds, WF
机构
[1] UNIV NACL AUTONOMA MEXICO, INST QUIM, MEXICO CITY 04510, DF, MEXICO
[2] UNIV TORONTO, TORONTO, ON M5S 1A1, CANADA
关键词
D O I
10.1016/S0957-4166(97)00271-1
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
We report the total synthesis of aziridine 3, carried out in a two-step method involving double Walden inversion at the carbon atom bearing the hydroxy group of (1R,2S)-(-)-norephedrine, 1, which was used as starting material. Compound 3 was obtained for the first time as a solid therefore allowing its unambiguous X-ray structure determination. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:2877 / 2879
页数:3
相关论文
共 14 条
[1]   STUDIES ON CHEMISTRY OF AZIRIDINE BORANES [J].
AKERFELDT, S ;
WAHLBERG, K ;
HELLSTROM, M .
ACTA CHEMICA SCANDINAVICA, 1969, 23 (01) :115-+
[2]   SYNTHETIC UTILITY OF AMINE BORANE REAGENTS IN THE REDUCTION OF ALDEHYDES AND KETONES [J].
ANDREWS, GC ;
CRAWFORD, TC .
TETRAHEDRON LETTERS, 1980, 21 (08) :693-696
[3]  
BARTNIK R, 1979, POL J CHEM, V53, P537
[4]   STEROIDS AND WALDEN INVERSION .11. ACETOLYSIS OF THE COPROSTANYL HALIDES [J].
BRIDGEWATER, RJ ;
SHOPPEE, CW .
JOURNAL OF THE CHEMICAL SOCIETY, 1953, (JUN) :1709-1715
[5]  
BROIS SJ, 1966, TETRAHEDRON LETT, P5113
[6]   STEREOCHEMISTRY AZIRIDINE RING EXPANSION SEQUENCES - NEW SYNTHESIS OF 2-OXAZOLIDONES [J].
HASSNER, A ;
BURKE, SS .
TETRAHEDRON, 1974, 30 (16) :2613-2621
[7]  
Kotera K., 1970, TETRAHEDRON, V26, P539
[8]   C-13 NMR-STUDY OF N-UNSUBSTITUTED AZIRIDINES .1. STERIC EFFECTS, PSEUDO-CONJUGATION [J].
MISON, P ;
CHAABOUNI, R ;
DIAB, Y ;
MARTINO, R ;
LOPEZ, A ;
LATTES, A ;
WEHRLI, FW ;
WIRTHLIN, T .
ORGANIC MAGNETIC RESONANCE, 1976, 8 (02) :79-89
[9]   2-sulfanilyl-aminothiazoline [J].
Raiziss, GW ;
Clemence, LW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1941, 63 :3124-3126
[10]   ON THE APPLICATION OF HAMILTONS RATIO TEST TO THE ASSIGNMENT OF ABSOLUTE-CONFIGURATION AND AN ALTERNATIVE TEST [J].
ROGERS, D .
ACTA CRYSTALLOGRAPHICA SECTION A, 1981, 37 (SEP) :734-741