用于合成β-单取代（仅Z-选择性）/二取代α-碘代-α,β-不饱和酯的3-烷氧基-2-炔-1-醇的碘代迈耶-舒斯特重排反应
Iodo Meyer-Schuster rearrangement of 3-alkoxy-2-yn-1-ols for β-mono (exclusively Z-selective)-/disubstituted α-iodo-α,β-unsaturated esters.
作者信息
Puri Surendra, Thirupathi Nuligonda, Sridhar Reddy Maddi
机构信息
Medicinal & Process Chemistry Division, CSIR-Central Drug Research Institute , BS-10/1, Sector 10, Jankipuram Extension, Sitapur Road, P.O. Box 173, Lucknow 226031, India.
出版信息
Org Lett. 2014 Oct 17;16(20):5246-9. doi: 10.1021/ol502224s. Epub 2014 Sep 26.
We herein present the iodo Meyer-Schuster rearrangement of 3-alkoxypropargyl alcohols for α-iodo-α,β-unsaturated esters using iodine or NIS in dichloromethane at ambient temperature. Substrates prepared from both aldehydes and ketones are found to be equally good feedstock for the reaction to produce β-mono- and -disubstituted products. Irrespective of the substitution, substrates prepared from aldehydes gave Z-isomers exclusively.
我们在此介绍了在室温下，于二氯甲烷中使用碘或N-碘代丁二酰亚胺（NIS），使3-烷氧基丙炔醇发生碘代迈耶-舒斯特重排反应生成α-碘代-α,β-不饱和酯。发现由醛和酮制备的底物作为反应原料同样良好，可生成β-单取代和双取代产物。无论取代情况如何，由醛制备的底物仅生成Z-异构体。
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