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Three-step synthesis of chiral spirocyclic oxaphospholenes

(2017) JOURNAL OF ORGANIC CHEMISTRY. 82(23). p.12439-12446
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Organization
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.
Keywords
CATALYZED PROPARGYLIC SUBSTITUTION, BRONSTED ACID CATALYST, TRANSFER HYDROGENATION, ALCOHOLS, IMINES, ALLENYLPHOSPHONATES, DERIVATIVES, ALKYLATION, OXIDATION, ALLENES

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Citation

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Chicago
Berton, Jan, Hadi Salemi, Jean-Luc Pirat, David Virieux, and Christian Stevens. 2017. “Three-step Synthesis of Chiral Spirocyclic Oxaphospholenes.” Journal of Organic Chemistry 82 (23): 12439–12446.
APA
Berton, J., Salemi, H., Pirat, J.-L., Virieux, D., & Stevens, C. (2017). Three-step synthesis of chiral spirocyclic oxaphospholenes. JOURNAL OF ORGANIC CHEMISTRY, 82(23), 12439–12446.
Vancouver
1.
Berton J, Salemi H, Pirat J-L, Virieux D, Stevens C. Three-step synthesis of chiral spirocyclic oxaphospholenes. JOURNAL OF ORGANIC CHEMISTRY. 2017;82(23):12439–46.
MLA
Berton, Jan et al. “Three-step Synthesis of Chiral Spirocyclic Oxaphospholenes.” JOURNAL OF ORGANIC CHEMISTRY 82.23 (2017): 12439–12446. Print.
@article{8545194,
  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.},
  author       = {Berton, Jan and Salemi, Hadi and Pirat, Jean-Luc and Virieux, David and Stevens, Christian},
  issn         = {0022-3263},
  journal      = {JOURNAL OF ORGANIC CHEMISTRY},
  keywords     = {CATALYZED PROPARGYLIC SUBSTITUTION,BRONSTED ACID CATALYST,TRANSFER HYDROGENATION,ALCOHOLS,IMINES,ALLENYLPHOSPHONATES,DERIVATIVES,ALKYLATION,OXIDATION,ALLENES},
  language     = {eng},
  number       = {23},
  pages        = {12439--12446},
  title        = {Three-step synthesis of chiral spirocyclic oxaphospholenes},
  url          = {http://dx.doi.org/10.1021/acs.joc.7b02227},
  volume       = {82},
  year         = {2017},
}

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