ANION REACTIONS OF 1,3-DITHIANE 1,3-DIOXIDE WITH CARBONYL-COMPOUNDS - HIGH DIASTEREOSELECTIVITY WITH AROMATIC-ALDEHYDES UNDER CONDITIONS OF EQUILIBRIUM CONTROL

被引：37
作者：
AGGARWAL, VK
FRANKLIN, R
MADDOCK, J
EVANS, GR
THOMAS, A
MAHON, MF
MOLLOY, KC
RICE, MJ
机构：
[1] UNIV BATH,SCH CHEM,BATH BA2 7AY,AVON,ENGLAND
[2] UNIV BATH,XRAY CRYSTALLOG UNIT,BATH BA2 7AY,AVON,ENGLAND
[3] ZENECA AGROCHEM,BRACKNELL RG12 6EY,BERKS,ENGLAND
来源：
JOURNAL OF ORGANIC CHEMISTRY | 1995年 / 60卷 / 07期
关键词：
D O I：
10.1021/jo00112a042
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
We have investigated the anion chemistry of trans-1,3-dithiane 1,3-dioxide (4) with aldehydes and ketones, and we have found that this reagent undergoes highly selective addition reactions with aromatic aldehydes but only when reactions are under equilibrium control (achieved using Na anion of 4). Other metals invetsigated (Li, Mg, Al, Ce, Ti) gave either poorer selectivity or caused decomposition of 4. Zn-4 did give improved selectivity at low temperature but only with aromatic aldehydes. Reactions with ketones were limited to those without a-branching. A model that accounts for the high diastereoselectivity observed with aromatic aldehydes is presented.
引用
收藏
页码：2174 / 2182
页数：9
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