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Solvent‐Assisted Diastereoselective Trimethylsilyl Cyanide Additions to Cyclic α‐Fluoro Ketones
Author(s) -
Pham Hao,
Davis Todd A.
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201201637
Subject(s) - chemistry , trimethylsilyl cyanide , cyanide , solvent , organic chemistry , cyanohydrin , acetonitrile , trimethylsilyl , medicinal chemistry , catalysis
This paper describes the solvent‐assisted addition of trimethylsilyl cyanide (TMSCN) to cyclic α‐fluorinated ketones. In DMF, this method gives TMS‐protected cyanohydrins in good yields (70–95 %) and with good selectivities ( dr up to 22:1), and the products are readily reduced to the corresponding fluorinated 1,2‐amino alcohols.