NOVEL STEROIDAL CHIRAL AUXILIARIES - ENANTIOSELECTIVE SYNTHESIS OF CHIRAL ALPHA-HYDROXY ACIDS

被引:8
作者
HUANG, DL
DRAPER, RW
机构
[1] Chemical Process Research Department, Schering-Plough Research Institute, Kenilworth
关键词
D O I
10.1016/S0040-4039(00)75783-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis is reported of three novel steroidal chiral auxiliaries (4) which were used to generate an alpha-hydroxy acid in high optical purity (90-98% ee).
引用
收藏
页码:661 / 662
页数:2
相关论文
共 10 条
[1]   ENANTIOSELECTIVE SYNTHESIS OF ALPHA-HYDROXY ACIDS AND BETA-HYDROXY ACIDS USING TRANS-2-PHENYLCYCLOHEXAN-1-OL AS CHIRAL AUXILIARY [J].
BASAVAIAH, D ;
BHARATHI, TK .
TETRAHEDRON LETTERS, 1991, 32 (28) :3417-3420
[2]   TRANS-2-PHENOXYCYCLOHEXAN-1-OL AS NEW CHIRAL AUXILIARY - SYNTHESIS OF CHIRAL ALPHA-HYDROXY ACIDS [J].
BASAVAIAH, D ;
BHARATHI, TK ;
KRISHNA, PR .
SYNTHETIC COMMUNICATIONS, 1992, 22 (06) :941-947
[3]   THE CHIRAL POOL AS A SOURCE OF ENANTIOSELECTIVE CATALYSTS AND AUXILIARIES [J].
BLASER, HU .
CHEMICAL REVIEWS, 1992, 92 (05) :935-952
[4]   HYDROBORATION .85. SYNTHESIS AND HYDROBORATION OF (-)-2-PHENYLAPOPINENE - COMPARISON OF MONO(2-PHENYLAPOISOPINOCAMPHEYL)BORANE WITH ITS 2-METHYL AND 2-ETHYL ANALOGS FOR THE CHIRAL HYDROBORATION OF REPRESENTATIVE ALKENES [J].
BROWN, HC ;
WEISSMAN, SA ;
PERUMAL, PT ;
DHOKTE, UP .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (04) :1217-1223
[5]   AN EFFICIENT PREPARATION OF (+)-TRANS-2-(ALPHA-CUMYL)CYCLOHEXANOL ((+)-TCC) - A PRACTICAL ALTERNATIVE TO (+)-8-PHENYLMENTHOL [J].
COMINS, DL ;
SALVADOR, JM .
TETRAHEDRON LETTERS, 1993, 34 (05) :801-804
[6]   REACTIONS OF A NEW OPTICALLY-ACTIVE ARYLPERHYDRONAPHTHALENOL BASED CHIRAL AUXILIARY [J].
HAMON, DPG ;
HOLMAN, JW ;
MASSYWESTROPP, RA .
TETRAHEDRON-ASYMMETRY, 1992, 3 (12) :1533-1536
[7]   RESOLUTION OF ALPHA-SUBSTITUTED MANDELIC-ACIDS VIA CHIRAL OXAZOLINES USING PRESSURIZED CHROMATOGRAPHY [J].
MEYERS, AI ;
SLADE, J .
JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (14) :2912-2914
[8]   NEW CHIRAL AUXILIARIES DERIVED FROM BETA-PINENE - THEIR USE IN THE ASYMMETRIC REDUCTION OF BETA-KETO-ESTERS [J].
VASCONCELLOS, ML ;
DANGELO, J ;
DESMAELE, D ;
COSTA, PRR ;
POTIN, D .
TETRAHEDRON-ASYMMETRY, 1991, 2 (05) :353-356
[9]  
WHITESELL JK, 1986, CHIMIA, V40, P318
[10]   CYCLOHEXYL-BASED CHIRAL AUXILIARIES [J].
WHITESELL, JK .
CHEMICAL REVIEWS, 1992, 92 (05) :953-964