1-Methyl-1H-tetrazol-5-yl (MT) sulfones in the Julia-Kocienski olefination: Comparison with the PT and the TBT sulfones
作者:Kaori Ando、Daiki Kawano、Daiki Takama、Yutaka Semii
DOI:10.1016/j.tetlet.2019.05.007
日期:2019.6
n-pentyl 1-methyl-1H-tetrazol-5-yl (MT) sulfone 1a in the Julia-Kocienski reactions were compared with those of the PT sulfone 1b and the TBT sulfone 1c. The improved stability of the anion derived from the n-pentyl MT sulfone 1a enhanced the efficiency of the olefination reactions and gave higher yields of the product alkenes 3 compared with the PT sulfone 1b. Especially high E-selectivity and high
比较了新制备的正戊基1-甲基-1 H-四唑-5-基(MT)砜1a在Julia-Kocienski反应中的稳定性和立体选择性,与PT砜1b和TBT砜1c的稳定性和立体选择性进行了比较。与PT砜1b相比,由正戊基MT砜1a衍生的阴离子的稳定性提高,提高了烯化反应的效率,并提高了烯烃3的产率。从与芳族醛和α,β-不饱和醛的反应中获得特别高的E-选择性和高产率。的选择性与PT砜1b相比,1a对碱抗衡离子的变化不太敏感。具有乙基或更长烷基链的MT砜的反应也以高收率选择性地产生了E-烯烃。