化学
分子内力
烯烃
醛
催化作用
联轴节(管道)
组合化学
药物化学
立体化学
有机化学
机械工程
工程类
作者
Sudipta Ghosh,Arnab Rooj,Rajesh Chakrabortty,Venkataraman Ganesh
标识
DOI:10.1021/acs.orglett.4c01428
摘要
We demonstrate for the first time a nickel-catalyzed diastereoconvergent reductive coupling of a heteroatom-attached allyl moiety with aldehydes, viz., O-allyl, O-cinnamyl salicylaldehydes, and others, to afford syn-chromanols exclusively. The reaction proceeds through a [2 + 2 + 1] oxidative cycloaddition involving the active catalyst. This method is applicable to both terminal and internal olefin substrates. The formal syntheses of CP-199.330, CP-199.331, and CP-85.958 have been demonstrated. Control experiments, mass spectrometric analysis, and DFT studies supported the plausible mechanism and the origin of exclusive syn-selectivity.
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