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Allylic Phosphorus Ylides Directly Generated from Alcohols with Water as the Only Byproduct
Peizhong Xie1, Weishan Fu1, Ying Wu1
1School of Chemistry and Molecular Engineering, Institute of Advanced Synthesis, Jiangsu National Synergetic Innovation Center for Advanced Materials , Nanjing Tech University , Nanjing 211816 , P. R. China.
Abstract:
A novel strategy for the preparation of allylic phosphorus ylides directly from Morita-Baylis-Hillman (MBH) alcohols in an environmentally benign manner was developed. With the assistance of a calcium catalyst, the SN2' process between phosphines and allylic alcohols occurred smoothly, delivering allylic phosphorus salts and calcium-stabilized hydroxide ions. Then, in situ deprotonation gave the allylic phosphorus ylides with water as the only byproduct. Functionalized 1,3-diene moieties can be conveniently obtained by trapping the ylides through a Wittig olefination.
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