OPENING OF OXABICYCLO[3.2.1]OCTENES WITH ORGANOLITHIUM REAGENTS - A ROUTE TO CYCLIC AND ACYCLIC COMPOUNDS WITH HIGH STEREOCONTROL

被引：43

作者：

LAUTENS, M

ABDELAZIZ, AS

LOUGH, A

机构：

[1] Department of Chemistry, University of Toronto, Ontario, M5S 1A1, Toronto

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1990年 / 55卷 / 19期

关键词：

D O I：

10.1021/jo00306a002

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

: A range of oxabicyclo[3.2.1]octenes has been found to undergo opening when treated with organolithium reagents. Up to five stereocenters are created in two steps. Oxidative cleavage leads to a stereocontrolled synthesis of polysubstituted cycloheptanediols. © 1990, American Chemical Society. All rights reserved.

引用

收藏

页码：5305 / 5306

页数：2

相关论文

共 24 条

[1] REGIOSPECIFIC AND STEREOSPECIFIC SYNTHESIS OF SUBSTITUTED CYCLOHEXENEDIOLS FROM 7-OXABICYCLO[2.2.1]HEPT-5-EN-2-OLS AND ORGANO-LITHIUM REAGENTS [J].

ARJONA, O ;

DELAPRADILLA, RF ;

GARCIA, E ;

MARTINDOMENECH, A ;

PLUMET, J .

TETRAHEDRON LETTERS, 1989, 30 (46) :6437-6440

[2]

ASHCROFT MR, 1988, ORG SYNTH, V6, P512

[3] LITHIUM TRI-SEC-BUTYLBOROHYDRIDE - NEW REAGENT FOR REDUCTION OF CYCLIC AND BICYCLIC KETONES WITH SUPER STEREOSELECTIVITY - REMARKABLY SIMPLE AND PRACTICAL PROCEDURE FOR CONVERSION OF KETONES TO ALCOHOLS IN EXCEPTIONALLY HIGH STEREOCHEMICAL PURITY [J].

BROWN, HC ;

KRISHNAMURTHY, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (20) :7159-+

[4] ADDITION OF BUTYLLITHIUMS TO BENZONORBORNADIENE AND 1,4-DIHYDRONAPHTHALENE 1,4-ENDO-OXIDE [J].

CAPLE, R ;

CHEN, GMS ;

NELSON, JD .

JOURNAL OF ORGANIC CHEMISTRY, 1971, 36 (19) :2874-&

[5] PROTECTION OF HYDROXYL GROUPS AS TERT-BUTYLDIMETHYLSILYL DERIVATIVES [J].

COREY, EJ ;

VENKATESWARLU, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (17) :6190-+

[6] OXYALLYLS IN SYNTHESIS - PREPARATION OF ANALOGS OF MUSCARINE AND ALPHA-MULTISTRIATIN [J].

COWLING, AP ;

MANN, J ;

USMANI, AA .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1981, (07) :2116-2119

[7]

FOEHLISCH B, 1981, J CHEM RES S, P246

[8] THE CYCLOADDITION OF ALLYL CATIONS TO 1,3-DIENES - GENERAL-METHOD FOR THE SYNTHESIS OF 7-MEMBERED CARBOCYCLES [J].

HOFFMANN, HMR .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1984, 23 (01) :1-19

[9] POLYHYDROXYLATED 7-MEMBERED CHIRAL BUILDING-BLOCKS - ASYMMETRIC-SYNTHESIS OF COMPACTIN ANALOGS [J].

JOHNSON, CR ;

SENANAYAKE, CH .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (04) :735-736

[10] RING-OPENING REACTIONS OF AN OXABICYCLIC COMPOUND WITH CUPRATES [J].

LAUTENS, M ;

DIFELICE, C ;

HUBOUX, A .

TETRAHEDRON LETTERS, 1989, 30 (49) :6817-6820