Enantiopure 3-amido or 3,3′-bisamido substituted 1,1′-bi-2-naphthols by anionic Fries rearrangements

被引:22
作者
Dennis, MR [1 ]
Woodward, S [1 ]
机构
[1] Univ Hull, Dept Chem, Kingston Upon Hull HU6 7RX, Yorks, England
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1998年 / 06期
关键词
D O I
10.1039/a708436f
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Mono- or di-carbamates of 1,1'-bi-2-naphthol ortholithiate with (BuLi)-Li-s-TMEDA, The resulting anions may either be captured by MeI or allowed to undergo anionic Fries rearrangement, Thus generalised two-step routes to mono-and di-(3-alkyl) or -(3-amido) substituted 2,2'-binapthols is demonstrated.
引用
收藏
页码:1081 / 1085
页数:5
相关论文
共 13 条
[1]   ASYMMETRIC-SYNTHESIS BY METAL BINAP CATALYSTS [J].
AKUTAGAWA, S .
APPLIED CATALYSIS A-GENERAL, 1995, 128 (02) :171-207
[2]  
BRUNNER H, 1992, NEW J CHEM, V16, P57
[3]   SIMPLE AND EFFICIENT RESOLUTION OF 1,1'-BI-2-NAPHTHOL [J].
CAI, DW ;
HUGHES, DL ;
VERHOEVEN, TR ;
REIDER, PJ .
TETRAHEDRON LETTERS, 1995, 36 (44) :7991-7994
[4]   EXPEDIENT ROUTE TO 3-SUBSTITUTED AND 3,3'-SUBSTITUTED 1,1'-BI-2-NAPHTHOLS BY DIRECTED ORTHO METALATION AND SUZUKI CROSS COUPLING METHODS [J].
COX, PJ ;
WANG, W ;
SNIECKUS, V .
TETRAHEDRON LETTERS, 1992, 33 (17) :2253-2256
[5]   MODELS FOR CHIRAL RECOGNITION IN MOLECULAR COMPLEXATION [J].
HELGESON, RC ;
TIMKO, JM ;
MOREAU, P ;
PEACOCK, SC ;
MAYER, JM ;
CRAM, DJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (21) :6762-6763
[6]   N,N,N',N'-tetraalkyl-2,2'-dihydroxy-1,1'-binaphthyl-3,3'-dicarboxamides: Novel chiral auxiliaries for asymmetric Simmons-Smith cyclopropanation of allylic alcohols and for asymmetric diethylzinc addition to aldehydes [J].
Kitajima, H ;
Ito, K ;
Aoki, Y ;
Katsuki, T .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1997, 70 (01) :207-217
[7]   Total syntheses of the angucyclinone antibiotics (+)-emycin A and (+)-ochromycinone [J].
Larsen, DS ;
OShea, MD ;
Brooker, S .
CHEMICAL COMMUNICATIONS, 1996, (02) :203-204
[8]  
MARUOKA K, 1991, SYNLETT, P793
[9]   A NEW CATALYTIC-SYSTEM FOR AEROBIC OXIDATIVE COUPLING OF 2-NAPHTHOL DERIVATIVES BY THE USE OF CUCL-AMINE COMPLEX - A PRACTICAL SYNTHESIS OF BINAPHTHOL DERIVATIVES [J].
NOJI, M ;
NAKAJIMA, M ;
KOGA, K .
TETRAHEDRON LETTERS, 1994, 35 (43) :7983-7984
[10]   DIRECTED ORTHO-METALATION REACTIONS - EXPEDIENT SYNTHESIS OF 3,3'-DISUBSTITUTED 1,1'-BI-(2-PHENOLS) (BIPOLS) [J].
PARSONS, AS ;
GARCIA, JM ;
SNIECKUS, VA .
TETRAHEDRON LETTERS, 1994, 35 (41) :7537-7540