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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Three-Step Synthesis of Chiral Spirocyclic Oxaphospholenes
Jan K E T Berton1,2, Hadi Salemi1,3, Jean-Luc Pirat2
1SynBioC Research Group, Department of Sustainable Organic Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University , Coupure Links 653, B-9000 Ghent, Belgium.
Abstract:
Chiral spirocylic oxaphospholenes were prepared in a three-step sequence from chiral pool terpenoid ketones. After addition of a metal acetylide, the resulting propargyl alcohols were converted stereoselectively into their allenylphosphonate counterparts. In the last step, they were conveniently cyclized into spirooxaphospholenes with one equivalent of iodine without purification. When starting from sterically hindered terpenes, allenylphosphonates were also easily obtained but showed to be unreactive or rearranged under these cyclization conditions.
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