On the chemoselectivity of formation of 2-(α-hydroxyalkyl)-2,5-dihydrofurans from allenic diols

被引：21

作者：

Aurrecoechea, JM ^{[1
]}

Solay, M ^{[1
]}

机构：

[1] Univ Basque Country, Fac Ciencias, Dept Quim Organ, E-48080 Bilbao, Spain

来源：

TETRAHEDRON | 1998年 / 54卷 / 15期

关键词：

D O I：

10.1016/S0040-4020(98)00111-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Ag(I)-promoted cyclization of 2,5-pentadiene-1,5-diols containing both a tertiary and a secondary or primary hydroxyl group, has been examined. In general, the reaction displays a preference for cyclization through the more hindered tertiary hydroxyl group, sometimes to the exclusion of alternative pathways involving secondary or primary carbinol centers. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：3851 / 3856

页数：6

共 16 条

[1] STEREOSELECTIVE SAMARIUM DIIODIDE-PROMOTED INTERMOLECULAR COUPLING OF ALKYNYLOXIRANES WITH KETONES - SYNTHESIS OF 2,3-PENTADIENE-1,5-DIOLS [J].

AURRECOECHEA, JM ;

SOLAY, M .

TETRAHEDRON LETTERS, 1995, 36 (14) :2501-2504

[2] CYCLOVIOLAXANTHIN (= (3S,5R,6R,3'S,5'R,6'R)-3,6-3',6'-DIEPOXY-5,6,5',6'-TETRAHYDRO-BETA,BETA-CAROTENE-5,5'-DIOL), A NOVEL CAROTENOID FROM RED PAPRIKA (CAPSICUM-ANNUUM) [J].

DELI, J ;

MOLNAR, P ;

TOTH, G ;

BAUMELER, A ;

EUGSTER, CH .

HELVETICA CHIMICA ACTA, 1991, 74 (04) :819-824

[3] STEREOSELECTIVE SYNTHESIS OF 3(2H)-DIHYDROFURANONES BY ADDITION OF LITHIATED METHOXYALLENE TO CHIRAL ALDEHYDES [J].

HORMUTH, S ;

REISSIG, HU .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (01) :67-73

[4] SYNTHESIS AND REACTIONS OF LITHIO DERIVATIVES OF 1-ALLENYLBENZOTRIAZOLE [J].

KATRITZKY, AR ;

VERIN, SV .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1995, 32 (01) :323-328

[5] TUMOR INHIBITORS .86. ISOLATION AND STRUCTURAL ELUCIDATION OF LIATRIN, A NOVEL ANTILEUKEMIC SESQUITERPENE LACTONE FROM LIATRIS-CHAPMANII [J].

KUPCHAN, SM ;

DAVIES, VH ;

FUJITA, T ;

COX, MR ;

RESTIVO, RJ ;

BRYAN, RF .

JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (10) :1853-1858

[6] STEREOSELECTIVE SYNTHESIS OF 2,5-DIHYDROFURANS BY SEQUENTIAL SN2' CLEAVAGE OF ALKYNYLOXIRANES AND AG+-CATALYZED CYCLIZATION OF THE ALLENYLCARBINOL PRODUCTS [J].

MARSHALL, JA ;

PINNEY, KG .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (25) :7180-7184

[7] SYNTHESIS OF THE PSEUDOPTERANE 2,5-FURANOCYCLIC RING-SYSTEM BY [2,3] WITTIG RING CONTRACTION OF BRIDGED FURAN AND DIHYDROFURAN PROPARGYLIC ETHERS [J].

MARSHALL, JA ;

YU, BC .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (02) :324-331

[8] SYNTHESIS OF ENANTIOENRICHED ALPHA-HYDROXY-ALPHA-ALLENYLACETIC ACIDS BY [2,3] WITTIG REARRANGEMENT OF ALPHA-(PROPARGYLOXY)ACETATES [J].

MARSHALL, JA ;

WANG, XJ .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (16) :4913-4918

[9] DIASTEREOSELECTIVE AND ENANTIOSELECTIVE SYNTHESIS OF ALLENYLCARBINOLS THROUGH S(E)2' ADDITION OF TRANSIENT NONRACEMIC PROPARGYLIC STANNANES TO ALDEHYDES [J].

MARSHALL, JA ;

YU, RH ;

PERKINS, JF .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (17) :5550-5555

[10] OBSERVATIONS REGARDING THE AG(I)-CATALYZED CONVERSION OF ALLENONES TO FURANS [J].

MARSHALL, JA ;

BARTLEY, GS .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (23) :7169-7171

← 1 2 →