A CONCISE ENANTIOSELECTIVE SYNTHESIS OF N-BOC-(S)-2-AMINOSUBERIC ACID

被引:10
作者
CASTEJON, P [1 ]
MOYANO, A [1 ]
PERICAS, MA [1 ]
RIERA, A [1 ]
机构
[1] UNIV BARCELONA,FAC QUIM,DEPT QUIM ORGAN,MARTI & FRANQUES 1-11,E-08028 BARCELONA,SPAIN
关键词
D O I
10.1080/00397919408011722
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The title compound has been enantioselectively obtained by a four-step process involving the catalytic asymmetric epoxidation of allyl alcohol 3, regio- and stereoselective oxirane opening with benzhydrylamine and one-pot oxidative cleavage-amine reprotection.
引用
收藏
页码:1231 / 1238
页数:8
相关论文
共 18 条
[1]  
BESTMANN HJ, 1978, TETRAHEDRON LETT, V36, P3329
[2]   REGIOSELECTIVE RING-OPENING OF CHIRAL EPOXYALCOHOLS BY PRIMARY AMINES [J].
CANAS, M ;
POCH, M ;
VERDAGUER, X ;
MOYANO, A ;
PERICAS, MA ;
RIERA, A .
TETRAHEDRON LETTERS, 1991, 32 (47) :6931-6934
[3]   A GREATLY IMPROVED PROCEDURE FOR RUTHENIUM TETRAOXIDE CATALYZED OXIDATIONS OF ORGANIC-COMPOUNDS [J].
CARLSEN, PHJ ;
KATSUKI, T ;
MARTIN, VS ;
SHARPLESS, KB .
JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (19) :3936-3938
[4]   ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETIC ACID, A VERSATILE REAGENT FOR DETERMINATION OF ENANTIOMERIC COMPOSITION OF ALCOHOLS AND AMINES [J].
DALE, JA ;
DULL, DL ;
MOSHER, HS .
JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (09) :2543-&
[5]  
EINHORN J, 1991, SYNLETT, V37
[6]   AMINO ACIDS AND PEPTIDES .57. A SYNTHESIS OF L-ALPHA-AMINOPIMELIC AND L-ALPHA-AMINOSUBERIC ACIK [J].
FARKASOVA, H ;
RUDINGER, J .
COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1965, 30 (09) :3117-+
[7]   CATALYTIC ASYMMETRIC EPOXIDATION AND KINETIC RESOLUTION - MODIFIED PROCEDURES INCLUDING INSITU DERIVATIZATION [J].
GAO, Y ;
HANSON, RM ;
KLUNDER, JM ;
KO, SY ;
MASAMUNE, H ;
SHARPLESS, KB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (19) :5765-5780
[8]   SYNTHESIS OF DL-ALPHA-AMINOSUBERIC ACID AND ITS OPTICAL RESOLUTION [J].
HASE, S ;
KIYOI, R ;
SAKAKIBA.S .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1968, 41 (05) :1266-+
[9]   SYNTHESIS OF A BIOLOGICALLY ACTIVE ANALOG OF DEAMINO-8-ARGININE-VASOPRESSIN WHICH DOES NOT CONTAIN A DISULPHIDE BOND [J].
HASE, S ;
MORIKAWA, T ;
SAKAKIBA.S .
EXPERIENTIA, 1969, 25 (12) :1239-&