Selective Synthesis of cis-α,β-Unsaturated Sulfoxides and Sulfides by the Horner-Wittig Reaction with Bis(2,2,2-trifluoroethyl)phosphono Sulfoxides and Aromatic Aldehydes
作者:Keisuki Kokin、Shuji Tsuboi、Jiro Motoyoshiya、Sadao Hayashi
DOI:10.1055/s-1996-4268
日期:1996.5
cis-α,β-Unsaturated sulfoxides were predominantly formed in the Horner-Wittig reaction with bis(2,2,2-trifluoroethyl)phosphono sulfoxides and aromatic aldehydes, while the reaction of the corresponding sulfides showed trans- or lower cis-selectivity. The reduction of cis-α,β-unsaturated sulfoxides with tributylphosphine in carbon tetrachloride gave cis-vinyl sulfides with retention of stereochemistry.
在与双(2,2,2-三氟乙基)磷酸亚磺酰和芳香醛的霍纳-维蒂格反应中,主要形成了顺-α,β-不饱和亚磺酰,而相应硫化物的反应则表现出反式或较低的顺选择性。用三丁基磷在四氯化碳中还原顺-α,β-不饱和亚磺酰产生了保持立体化学的顺-乙烯基硫化物。