Scope of the nickel catalyzed asymmetric reductive ring opening reaction. Synthesis of enantiomerically enriched cyclohexenols.

被引：44

作者：

Lautens, M ^{[1
]}

Rovis, T ^{[1
]}

机构：

[1] Univ Toronto, Dept Chem, Laser Miller Labs, Toronto, ON M5S 1A1, Canada

来源：

TETRAHEDRON | 1998年 / 54卷 / 07期

关键词：

D O I：

10.1016/S0040-4020(97)10211-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Subjecting a variety of oxabicyclo[2.2.1]heptenes to diisobutylaluminum hydride (DIBAL-H) in the presence of a catalytic amount of Ni(COD)(Z) and (R)-BINAP results in a highly enantioselective ring opening to generate cyclohexenols with ee's typically greater than 90%. The scope of this reaction has been delineated and alternative nickel catalysts have been examined which are less sensitive than NI(COD)(2). (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：1107 / 1116

页数：10

共 23 条

[1] CONDURITOLS AND RELATED-COMPOUNDS [J].

BALCI, M ;

SUTBEYAZ, Y ;

SECEN, H .

TETRAHEDRON, 1990, 46 (11) :3715-3742

[2] STEREOSPECIFIC BENZYLIC HYDROXYLATION OF BICYCLIC ALKENES BY PSEUDOMONAS-PUTIDA - ISOLATION OF (+)-R-1-HYDROXY-1,2-DIHYDRONAPHTHALENE, AN ARENE HYDRATE OF NAPHTHALENE FROM METABOLISM OF 1,2-DIHYDRONAPHTHALENE [J].

BOYD, DR ;

MCMORDIE, RAS ;

SHARMA, ND ;

DALTON, H ;

WILLIAMS, P ;

JENKINS, RO .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (06) :339-340

[3] Dioxygenase-catalysed oxidation of dihydronaphthalenes to yield arene hydrate and cis-dihydro naphthalenediols [J].

Boyd, DR ;

Sharma, ND ;

Kerley, NA ;

McMordie, RAS ;

Sheldrake, GN ;

Williams, P ;

Dalton, H .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (01) :67-74

[4]

Chiu P, 1997, TOP CURR CHEM, V190, P1

[5]

DUMORTIER L, 1992, SYNLETT, P243

[6]

DUMORTIER L, 1992, SYNLETT, P245

[7]

Eisch J. J., 1991, COMPREHENSIVE ORGANI, V8, P733, DOI 10.1016/B978-0-08-052349-1.00244-4

[8] NICKEL-CATALYZED HYDRALUMINATION OF ALKYNES AND NICKEL EFFECT IN ZIEGLER DIMERIZATION OF ETHYLENE [J].

EISCH, JJ ;

FOXTON, MW .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1968, 12 (03) :P33-&

[9] ORGANOMETALLIC COMPOUNDS OF GROUP-III .39. KINETIC AND STEREOCHEMICAL FACTORS IN THE HYDRALUMINATION OF ALKENES AND THE CONFIGURATIONAL STABILITY OF THE RESULTING CARBON-ALUMINUM BOND [J].

EISCH, JJ ;

FICHTER, KC .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1983, 250 (01) :63-81

[10] Aluminum-nickel bonded intermediates in the Ziegler Nickel Effect: Mechanistic support from catalyzed hydroalumination and carbalumination reactions [J].

Eisch, JJ ;

Ma, X ;

Singh, M ;

Wilke, G .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1997, 527 (1-2) :301-304

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