[4+2] and [2+2] photocycloadditions of 1,2-diketones to glyeal and hydroxyglycal esters

被引：13

作者：

Lichtenthaler, FW ^{[1
]}

Weimer, T ^{[1
]}

Immel, S ^{[1
]}

机构：

[1] Tech Univ Darmstadt, Clemens Schop Inst Organ Chem & Biochem, D-64287 Darmstadt, Germany

来源：

TETRAHEDRON-ASYMMETRY | 2004年 / 15卷 / 17期

关键词：

D O I：

10.1016/j.tetasy.2004.07.019

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Photocycloadditions of phenanthrenequinone 1 and acenaphthenequinone 16 to 3,4,6-tri-O-acetyl-D-glucal proceeded with distinctly different regioselectivities: 1 preferentially adds with both carbonyl oxygens to give the [4+2] cycloadduct, a 1-O,2-O-annelated alpha-D-glucoside (50% [Chem. Ber. 1952, 85, 531]), while 16 reacts with only one carbonyl group to exclusively yield the [2+2] addition product, a 1-C,2-O-oxetano-alpha-D-glucoside (86%). 2-Hydroxyglucal esters 11 and 12 also undergo photoadditions with 1 to give the cis-1,4-dioxane-fused cycloadducts 13 and 14, whilst 16 fails to react. Structural and configurational assignments rest on NMR data and an X-ray analysis of spiro-pyranooxetane 18. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：2703 / 2709

页数：7

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