La(OTf)3-catalyzed 7-endo and 8-endo selective cyclizations of hydroxy epoxides

被引：37

作者：

Fujiwara, K ^{[1
]}

Mishima, H ^{[1
]}

Amano, A ^{[1
]}

Tokiwano, T ^{[1
]}

Murai, A ^{[1
]}

机构：

[1] Hokkaido Univ, Grad Sch Sci, Div Chem, Sapporo, Hokkaido 060, Japan

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 5-6期

关键词：

D O I：

10.1016/S0040-4039(97)10557-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Endo selective intramolecular cyclization has been achieved in 5, 6-epoxy-5-methoxymethyl-1-heptanol and 6, 7-epoxy-6-methoxymethyl-3-octen-1-ol systems by the chelation of La(OTf)(3) between the oxygen atoms of the epoxide and methoxymethyl groups, affording 3-hydroxyoxepane and 3-hydroxy-5-oxocene derivatives, respectively. (C) 1997 Elsevier Science Ltd. All rights reserved.

引用

页码：393 / 396

页数：4

共 27 条

[1] RULES FOR RING-CLOSURE [J].

BALDWIN, JE .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1976, (18) :734-736

[2] SELECTIVE TRANSFORMATIONS OF 2,3-EPOXY ALCOHOLS AND RELATED DERIVATIVES - STRATEGIES FOR NUCLEOPHILIC-ATTACK AT CARBON-3 OR CARBON-2 [J].

BEHRENS, CH ;

SHARPLESS, KB .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (26) :5696-5704

[3] TI(O-I-PR)4-MEDIATED NUCLEOPHILIC OPENINGS OF 2,3-EPOXY ALCOHOLS - A MILD PROCEDURE FOR REGIOSELECTIVE RING-OPENING [J].

CARON, M ;

SHARPLESS, KB .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (09) :1557-1560

[4] TOTAL SYNTHESIS OF (+/-)-ZOAPATANOL [J].

CHEN, R ;

ROWAND, DA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (21) :6609-6611

[5] A TOTAL SYNTHESIS OF ZOAPATANOL [J].

COOKSON, RC ;

LIVERTON, NJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (08) :1589-1595

[6] USE OF LANTHANIDE(III) IONS AS CATALYSTS FOR THE REACTIONS OF AMINES WITH NITRILES [J].

FORSBERG, JH ;

SPAZIANO, VT ;

BALASUBRAMANIAN, TM ;

LIU, GK ;

KINSLEY, SA ;

DUCKWORTH, CA ;

POTERUCA, JJ ;

BROWN, PS ;

MILLER, JL .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (06) :1017-1021

[7] LA(OTF)(3)-CATALYZED 6-ENDO EPOXIDE OPENING OF 4,5-EPOXY-4-METHOXYMETHYL-1-HEXANOLS [J].

FUJIWARA, K ;

TOKIWANO, T ;

MURAI, A .

TETRAHEDRON LETTERS, 1995, 36 (44) :8063-8066

[8] REGIOSELECTIVE TITANIUM-MEDIATED RING OPENINGS OF 2,3-EPOXY ALCOHOLS WITH DIALKYLAMINE HYDROHALIDES [J].

GAO, LX ;

MURAI, A .

CHEMISTRY LETTERS, 1989, (02) :357-358

[9] HIGHLY REGIOSELECTIVE RING-OPENING OF 2,3-EPOXY ALCOHOL METHANESULFONATES [J].

GAO, LX ;

SAITOH, H ;

FENG, F ;

MURAI, A .

CHEMISTRY LETTERS, 1991, (10) :1787-1790

[10] ANTIBODY CATALYSIS OF A DISFAVORED CHEMICAL TRANSFORMATION [J].

JANDA, KD ;

SHEVLIN, CG ;

LERNER, RA .

SCIENCE, 1993, 259 (5094) :490-493

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