3 years ago
Three-Step Synthesis of Chiral Spirocyclic Oxaphospholenes
Hadi Salemi, Jean-Luc Pirat, David Virieux, Christian V. Stevens, Jan K. E. T. Berton
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.
Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b02227
DOI: 10.1021/acs.joc.7b02227
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