A modular approach to nonracemic cyclo-BINOLs.: Preparation of symmetrically & unsymmetrically substituted ligands

被引:36
作者
Lipshutz, BH [1 ]
Shin, YJ [1 ]
机构
[1] Univ Calif Santa Barbara, Dept Chem, Santa Barbara, CA 93106 USA
基金
美国国家卫生研究院;
关键词
D O I
10.1016/S0040-4039(98)01468-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new series of substituted cyclo-BINOLs is described, constructed using individually fashioned naphthol units which are tethered and oxidized to arrive at nonracemic materials. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:7017 / 7020
页数:4
相关论文
共 15 条
[1]   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
[2]   OXIDATIVE COUPLING OF PHENOLS [J].
DEWAR, MJS ;
NAKAYA, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (25) :7134-&
[3]  
Hughes D.L., 1992, ORG REACT, V42, P335, DOI [10.1002/0471264180.OR042.02, DOI 10.1002/0471264180.OR042.02]
[4]   A new powerful and practical BLA catalyst for highly enantioselective Diels-Alder reaction: An extreme acceleration of reaction rate by Bronsted acid [J].
Ishihara, K ;
Kurihara, H ;
Yamamoto, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (12) :3049-3050
[5]   BRONSTED ACID ASSISTED CHIRAL LEWIS-ACID (BLA) CATALYST FOR ASYMMETRIC DIELS-ALDER REACTION [J].
ISHIHARA, K ;
YAMAMOTO, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (04) :1561-1562
[6]   CATALYTIC ASYMMETRIC DIHYDROXYLATION [J].
KOLB, HC ;
VANNIEUWENHZE, MS ;
SHARPLESS, KB .
CHEMICAL REVIEWS, 1994, 94 (08) :2483-2547
[7]   HOST-GUEST COMPLEXATION .23. HIGH CHIRAL RECOGNITION OF AMINO-ACID AND ESTER GUESTS BY HOSTS CONTAINING ONE CHIRAL ELEMENT [J].
LINGENFELTER, DS ;
HELGESON, RC ;
CRAM, DJ .
JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (02) :393-406
[8]   A potentially general intramolecular biaryl coupling approach to optically pure 2,2'-BINOL analogs [J].
Lipshutz, BH ;
James, B ;
Vance, S ;
Carrico, I .
TETRAHEDRON LETTERS, 1997, 38 (05) :753-756
[9]   CHIRAL 1,1'-BINAPHTHYL MOLECULAR CLEFTS FOR THE COMPLEXATION OF EXCITATORY AMINO-ACID DERIVATIVES [J].
MARTINBOROUGH, E ;
DENTI, TM ;
CASTRO, PP ;
WYMAN, TB ;
KNOBLER, CB ;
DIEDERICH, F .
HELVETICA CHIMICA ACTA, 1995, 78 (05) :1037-1066
[10]   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