Tetrahedron p. 10325 - 10340 (1999)
Update date:2022-08-04
Topics:
Shibuya, Akira
Okada, Midori
Nakamura, Yuko
Kibashi, Mie
Horikawa, Hiroaki
Taguchi, Takeo
Preparation of methylenedifluorocyclopropanes 2 through the β- elimination reaction promoted by difluorocyclopropyl anion formed by cleavage of C-Si bond with TBAF is described. Base-catalyzed isomerization of 2 to difluorocyclopropene 11 shows the latter structure thermodynamically more stable in contrast to non-fluorinated cases. Application of this method to the synthesis of methylenedifluorocyclopropylglycine (F2MCPG) derivative 17 is also presented.
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Doi:10.1002/chem.201603449
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