Substituent Effect on the Asymmetric Induction with (1R,2S,5R)-and (1S,2R,5S)-menthol Auxiliaries

被引：0
作者：
Er, Mustafa [1 ]
Coskun, Necdet [2 ]
机构：
[1] Mus Alparslan Univ, Dept Chem, TR-49100 Mus, Turkey
[2] Uludag Univ, Dept Chem, TR-16059 Gorukle, Turkey
来源：
JOURNAL OF THE CHEMICAL SOCIETY OF PAKISTAN | 2010年 / 32卷 / 02期
关键词：
C-13; SIDE-CHAIN; DARZENS REACTION; TAXOL; DERIVATIVES; EPOXIDATION; PACLITAXEL; OLEFINS;
D O I：
暂无
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Substituted benzaldehydes reacts in cis-diastereoselective manner with menthyl haloacetates in the presence of phase transfer catalyst and a base in THF at room temperature to, give the corresponding 3-aryloxirane-2-carboxylates (2/3a-h) in moderate to high yields. The magnitude of asymmetric induction in the latter reaction was quantified by a Hammett type equation log(2/3)(X) = p sigma(1) + log(2/3)(X=H). The stereochemistry of compounds 2 and 3 was elucidated by correlation with (4S,5R)-2,4-dipheny1-4,5-dihydrooxazole-5-carboxylic acid (+)-8 as well as its enantiomer (-)-8.
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页码：198 / 208
页数：11
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