化学
环氧化物
叶立德
樟脑
重氮
苯甲醛
双环分子
有机化学
硫化物
盐(化学)
催化作用
作者
Varinder K. Aggarwal,Cristina Aragoncillo,C. L. Winn
出处
期刊:Synthesis
[Georg Thieme Verlag KG]
日期:2005-01-01
卷期号: (8): 1378-1382
被引量:10
标识
DOI:10.1055/s-2004-834885
摘要
A practical route to epoxides with control of the relative and absolute stereochemistry has been developed, allowing epoxides to be readily prepared on a 20 mmol scale by generating the reactive intermediate (the diazo compound) in situ from benzaldehyde tosylhydrazone sodium salt. In this paper, we describe the optimum conditions for three procedures to obtain the desired racemic and enantiomerically enriched epoxides (Scheme [1] ). High diastereoselectivities (98-100%) and very high yields of epoxide were obtained. Asymmetric epoxidation was carried out using the chiral camphor-derived [2.2.1] bicyclic sulfide 4 and the desired epoxide was obtained with excellent enantioselectivity (94%).
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