ACID-PROMOTED REACTION OF CYCLIC ALLYLIC DIOLS WITH CARBONYL-COMPOUNDS - STEREOSELECTIVE RING-ENLARGING TETRAHYDROFURAN ANNULATIONS

被引：60

作者：

BROWN, MJ ^{[1
]}

HARRISON, T ^{[1
]}

HERRINTON, PM ^{[1
]}

HOPKINS, MH ^{[1
]}

HUTCHINSON, KD ^{[1
]}

MISHRA, P ^{[1
]}

OVERMAN, LE ^{[1
]}

机构：

[1] UNIV CALIF IRVINE,DEPT CHEM,IRVINE,CA 92717

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1991年 / 113卷 / 14期

关键词：

SELECTIVE SYNTHESIS; HYDROXY KETONES; CYCLIZATION; REDUCTION; ACETALS; TRIACETOXYBOROHYDRIDE; MECHANISM; IONS;

D O I：

10.1021/ja00014a031

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A wide variety of cis-fused hexahydrocyclopenta[b]furan-4-ones (3, n = 0), hexahydro-4(2H)-benzofuranones (3, n = 1), and octahydrocyclohepta[b]furan-4-ones (3, n = 2) can be prepared with high levels of stereocontrol by the title reaction. The scope and limitations of this powerful new method for assembling polycyclic ethers are explored in detail. Conformational analysis of potential oxabicyclo[4.4.0]decanyl, oxabicyclo[4.3.0]nonanyl, and oxabicyclo[4.2.0]octanyl cation intermediates allows the stereochemical outcome of the title reaction to be predicted.

引用

页码：5365 / 5378

页数：14

共 35 条

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