THE CHIRAL AMINO ALCOHOL, CIS-2-AMINO-1-ACENAPHTHENOL - SYNTHESIS, RESOLUTION, AND APPLICATION TO THE DIASTEREOSELECTIVE [2,3]-WITTIG REARRANGEMENT

被引:16
作者
SUDO, A [1 ]
HASHIMOTO, Y [1 ]
KIMOTO, H [1 ]
HAYASHI, K [1 ]
SAIGO, K [1 ]
机构
[1] UNIV TOKYO,FAC ENGN,DEPT CHEM & BIOTECHNOL,BUNKYO KU,TOKYO 113,JAPAN
关键词
D O I
10.1016/0957-4166(94)80175-4
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The chiral amino alcohol, cis-2-amino-1-acenaphthenol, was synthesized, and resolved by a simple procedure. This new chiral amino alcohol was converted into an oxazoline derivative and applied as a chiral auxiliary to the diastereoselective [2,3]-Wittig rearrangement.
引用
收藏
页码:1333 / 1346
页数:14
相关论文
共 29 条
[21]  
OPPOLZER W, 1987, TETRAHEDRON, V43, P1969, DOI 10.1016/S0040-4020(01)86780-6
[22]   CHIRAL SEMICORRINS AND RELATED NITROGEN-HETEROCYCLES AS LIGANDS IN ASYMMETRIC CATALYSIS [J].
PFALTZ, A .
ACCOUNTS OF CHEMICAL RESEARCH, 1993, 26 (06) :339-345
[23]   ENANTIOSELECTIVE ADDITION OF CHIRALLY MODIFIED METHYLTITANIUM REAGENTS TO AROMATIC-ALDEHYDES [J].
REETZ, MT ;
KUKENHOHNER, T ;
WEINIG, P .
TETRAHEDRON LETTERS, 1986, 27 (47) :5711-5714
[24]   OPTICAL RESOLUTION OF 2-AMINO-1,2-DIPHENYLETHANOL BY PREFERENTIAL CRYSTALLIZATION AND ITS UTILIZATION IN FRACTIONAL CRYSTALLIZATION AND ENANTIOSELECTIVE REDUCTION OF PROCHIRAL KETONES [J].
SAIGO, K ;
OGAWA, S ;
KIKUCHI, S ;
KASAHARA, A ;
NOHIRA, H .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1982, 55 (05) :1568-1573
[25]   OPTICAL RESOLUTION OF ERYTHRO-2-AMINO-1,2-DIPHENYLETHANOL BY RECIPROCAL CRYSTALLIZATION OF THE DIASTEREOMERIC SALTS WITH (-)-MANDELIC ACID ON ALTERNATE SEEDING [J].
SAIGO, K ;
SUGIURA, I ;
SHIDA, I ;
TACHIBANA, K ;
HASEGAWA, M .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1986, 59 (09) :2915-2916
[26]   APPLICATION OF ERYTHRO-2-METHOXY-1,2-DIPHENYLETHYLAMINE TO ENANTIOSELECTIVE ALKYLATION OF CYCLOHEXANONE [J].
SAIGO, K ;
KASAHARA, A ;
OGAWA, S ;
NOHIRA, H .
TETRAHEDRON LETTERS, 1983, 24 (05) :511-512
[27]   A NEW CHIRAL AUXILIARY FOR ASYMMETRIC THERMAL-REACTIONS - HIGH STEREOCONTROL IN RADICAL-ADDITION, ALLYLATION, AND ANNULATION REACTIONS [J].
STACK, JG ;
CURRAN, DP ;
GEIB, SV ;
REBEK, J ;
BALLESTER, P .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (18) :7007-7018
[28]   CONFORMATIONALLY RIGID ACYCLIC 2,2,6,6-TETRAMETHYL-3,5-HEPTANEDIOL (TMHDIOL) DERIVATIVE AS A NEW CLASS OF CHIRAL AUXILIARIES [J].
SUZUKI, I ;
KIN, H ;
YAMAMOTO, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (22) :10139-10146
[29]   CATALYTIC ENANTIOSELECTIVE CONJUGATE ADDITION OF CHIRAL ALKOXYDIMETHYLCUPRATE TO (E)-CYCLOPENTADEC-2-ENONE [J].
TANAKA, K ;
MATSUI, J ;
SUZUKI, H ;
WATANABE, A .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (10) :1193-1194