DIRECTED ORTHO-METALATION REACTIONS - EXPEDIENT SYNTHESIS OF 3,3'-DISUBSTITUTED 1,1'-BI-(2-PHENOLS) (BIPOLS)

被引：19

作者：

PARSONS, AS ^{[1
]}

GARCIA, JM ^{[1
]}

SNIECKUS, VA ^{[1
]}

机构：

[1] UNIV WATERLOO,GUELPH WATERLOO CTR GRAD WORK CHEM,WATERLOO N2L 3G1,ON,CANADA

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 41期

关键词：

D O I：

10.1016/S0040-4039(00)78337-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Metalation-electrophile quench of the 1,1'-bi-(2-biphenol) bis OCONEt(2) and OMOM derivatives 1a-b provides a general route to 3,3'-disubstituted products 2a-b; dianionic ortho-Fries rearrangement of la furnishes, after acetylation, the 3,3'-bisamide 4 while Suzuki and Negishi cross coupling of 2a (E = I and ZnBr) affords 3,3'-diaryl derivatives 5a-b in good yields.

引用

页码：7537 / 7540

页数：4

共 32 条

[1] CATALYTIC ASYMMETRIC-SYNTHESIS OF CYCLOPROPANE-CARBOXYLIC ACIDS - AN APPLICATION OF CHIRAL COPPER CARBENOID REACTION [J].

ARATANI, T .

PURE AND APPLIED CHEMISTRY, 1985, 57 (12) :1839-1844

[2]

BRANSMA I, 1990, PREPARATIVE POLAR OR, V2, P7

[3] REGIOSELECTIVE AND ENANTIOSELECTIVE CATALYTIC EPOXIDATION OF CONJUGATED POLYENES - FORMAL SYNTHESIS OF LTA(4) METHYL-ESTER [J].

CHANG, S ;

LEE, NH ;

JACOBSEN, EN .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (25) :6939-6941

[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] Dibenzofuran. XIX. Derivatives of 2,2'-dihydroxybiphenyl [J].

Gilman, H ;

Swiss, J ;

Cheney, LC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1940, 62 :1963-1967

[6] ENANTIOSELECTIVE SYNTHESIS - INTRODUCTION [J].

GLADYSZ, JA ;

MICHL, J .

CHEMICAL REVIEWS, 1992, 92 (05) :739-739

[7]

GODFRIED JH, 1993, TETRAHEDRON-ASYMMETR, V4, P1625

[8] CATALYTIC ASYMMETRIC EPOXIDATION OF UNFUNCTIONALIZED OLEFINS USING CHIRAL (SALEN)MANGANESE(III) COMPLEXES [J].

IRIE, R ;

NODA, K ;

ITO, Y ;

MATSUMOTO, N ;

KATSUKI, T .

TETRAHEDRON-ASYMMETRY, 1991, 2 (07) :481-494

[9] ASYMMETRIC EPOXIDATION USING CHIRAL SALEN COMPLEXES [J].

IRIE, R .

JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 1993, 51 (05) :412-420

[10] DIRECTED ORTHO METALATION OF TERTIARY AROMATIC AMIDES - A NEW N-HETERO-RING ANNELATION METHOD AND SYNTHESIS OF PHENANTHRO-QUINOLIZIDINE AND PHENANTHRO-INDOLIZIDINE ALKALOIDS [J].

IWAO, M ;

MAHALANABIS, KK ;

WATANABE, M ;

DESILVA, SO ;

SNIECKUS, V .

TETRAHEDRON, 1983, 39 (12) :1955-1962

← 1 2 3 4 →