Synthesis of 2-vinylcyclopentanols by SmI2/Pd(0)-promoted carbohydrate ring-contraction.

被引：20

作者：

Aurrecoechea, JM ^{[1
]}

López, B ^{[1
]}

机构：

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

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 18期

关键词：

D O I：

10.1016/S0040-4039(98)00317-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The treatment of methyl 5-vinylpyranosides with SmI2/cat. Pd(0) results in the formation of 2-vinylcyclopentanols. This process represents a new direct transformation of a carbohydrate structure into a functionalized carbocycle. The salient feature of this reaction is the preferred trans-relationship observed between the newly created stereocenters which is opposite to that found with alternative methodology. Moderate diastereoselectivities combined with high chemical yields provide preparatively useful yields of the major carbocyclic trans-diastereomer. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：2857 / 2860

页数：4

共 33 条

[11] THE CONVERSION OF CARBOHYDRATE-DERIVATIVES INTO FUNCTIONALIZED CYCLOHEXANES AND CYCLOPENTANES [J].

FERRIER, RJ ;

MIDDLETON, S .

CHEMICAL REVIEWS, 1993, 93 (08) :2779-2831

[12]

Grove JJC, 1996, TETRAHEDRON LETT, V37, P5817

[13]

Grove JJC, 1996, TETRAHEDRON LETT, V37, P1305

[14]

HANZAWA Y, 1995, SYNLETT, P299

[15] ZIRCONIUM-MEDIATED, HIGHLY DIASTEREOSELECTIVE RING CONTRACTION OF CARBOHYDRATE-DERIVATIVES - SYNTHESIS OF HIGHLY FUNCTIONALIZED, ENANTIOMERICALLY PURE CARBOCYCLES [J].

ITO, H ;

MOTOKI, Y ;

TAGUCHI, T ;

HANZAWA, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (19) :8835-8836

[16] Chiral cyclopentane-based mimics of D-myo-inositol 1,4,5-trisphosphate from D-glucose [J].

Jenkins, DJ ;

Riley, AM ;

Potter, BVL .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (22) :7719-7726

[17] Intramolecular reaction of (gamma-alkoxyallyl)stannane with aldehyde: Origin of the stereoselectivities [J].

Kadota, I ;

Kawada, M ;

Gevorgyan, V ;

Yamamoto, Y .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (21) :7439-7446

[18]

Kawatsura M, 1996, SYNLETT, P373

[19]

KAWATSURA M, 1995, SYNLETT, P729

[20] SAMARIUM(II) IODIDE PROMOTED INTERMOLECULAR KETONE OLEFIN COUPLINGS CHELATION-CONTROLLED BY ALPHA-HYDROXYL GROUPS [J].

KAWATSURA, M ;

MATSUDA, F ;

SHIRAHAMA, H .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (23) :6900-6901

← 1 2 3 4 →